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DAI HOC o u 6 c (;f A HA NAI

BAO CAO KfiT QUA THUC HI$N

Dfi TAI DAc BlfiT CA'P DHQG: 2001 - 200.1

T«n dt

Ml •

"NGHIEN CtJtJ

T 6 N G HOP, CAU

TRUC VA HOAT TfNH

SINH HOC COA CAC HOP CHAT TlTONG TV FLA VON,

C6 CHtTA

NHAN DI

VONG"

M&s6 : QG.01-02

Chu i.hi«m d^ m: GS. TSKH. Nguyin Minh Thdo

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PHAN MO DAU

MUC LUC

Trang

PHAN Md DAU '

Danh sdch nhChig ngUiVi tham gia dC tai

3

Danh muc cac bang s6 li6u ^

Danh miic c^c hinh ^

TOM TAT NHUNG KET QUA CHINH ^

L Ke't qua v6 mat khoa hoc 4

2. K6t qua phuc vu thuc te 5

3. K6x qua dao tao 5

4. K6'l qua niing cao tiOm luc khoa hoc 6

5. Tmh hinh su dung kinh phi 6

ABSTRACT 7

PHAN N O I DUNG CHINH 8

I. DillvAiid^ 8

II. Tdng quan cac vA'n de nghien cuu 9

2.1 Ve pli.ln inij.' (.huven vj I rii*s 9

2.2 Ve cac xeton a. (3-khong no 10

2.3 Vrti net v6 riavon va flavonoit 11

IIL Phuang phap nghien cuu va Ihuc nghiem 12

3.1 Pliuotig phap xac djnh cau tao do tinh khiet yh hoat tfnh sinh hgc ciia 12

cac hgp cliiit tdng hop dugc

3.2 Tdng hgp cac este ciia phenol va thuc hien phan ung chuyen vi Fries 12

cua chiing

'5-3 HiU(/ng phap chung tdng hgp cac xeton a, \\- khAng no: 14

3.4 Pliuang phap chung tdng hgp cac hgp chat tuong tu flavon 19

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24 4.1 Axetyl hoa c^c phenol vh chuyen vj Fries cua chiing 24

4.2 Tdng hgp cdc xclon a. \\- khOng no 25

4.3 Tdng hgp cac hgp chAt tuctng tir flavon co dura nhAn di vong 25

4.4 Tdng hgp cdc hgp chflft kieu pira/olin chi'fa nhrui <li vong 26

4.5 Tinh toan hoa lugng tir 26

4.6 Thdm do hoat tfnh sinh hoc 26

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I H C N G N G U O I

THAM (ilA DE TAI

1. Nguyen Minh Thao - GS. TSKH - Truong Dai hoc Khoa hoc Tu nhicn- DHQG HN.

2. Pham Van Phong - ThS. - Trucmg Dai hgc Khoa hgc Tu nhien- DHQG HN.

3. M6t s6' hgc vien cao hgc va sinh vien.

DANH MUC CAC BANC; SO LI$U

Bang I: Cac san phiim phan ihig chuyen vi Irics

Bang 2: Cdc xeton a. p- khAng no day agienol va iso(rgicnol (E,.;)

Bang 3: Cac xeton a. P- khong no di tir resoxinol (K, s va DKr.. m)

Bang 4: Cac xeton a. P- khong no di ti^ hidroquinon (H,.?)

Bang 5: Cac xeton a, P- khdng-no di ti^ 7- hidroxi- 8- axelylquinolin (Q, 4)

Bang 6: Cac xeton a, p-kh6ng no di lii axit dehidroaxctic ( D H A i n )

Bang 7: Cdc xeton a, P- khdng no di tir 7- hidroxi- 4- metylcumarin (C|.g)

Bang 8: Cdc hgp ch^t tucmg tu flavon di tir agienol va iso(tgicnol

{FEU.)

Bang 9: Cdc hgp chat tuong tu flavon di tu resoxinol (F,i,.s va

F„K6..>)

Bang 10: Cdc hop chat tuong lu flavon di lu hidrcxjuinon (F,,, 0

Bang 11: Cac hgp chat luang tu llavon di lu hidroxiquinolin (F,^,^)

Bang 12: Cac luirp chAI tucmg tu flavon di Iff axit dcliidroaxclic

(F„HA

112)

Bang 13: Cac pira/t)lin chua lutj) phdn (tgicnol v;i isoofgicnol (IVi (d

Bang 14: Cdc pirazolin chira hgp phAn resoxinol (P,(, ^ va F*,,^^, .,):

Bang 15: Cdc pira/olin chua hgp phdn hidrocpiinon (P,,, 0

Bang 16: C{ic piia/olin cliu;i hgp phdn axil deiiidroaxclic

(PDHA,

,,)

Bang 17: Cac pinizolin clura vong tiuinolin (P^i i)

Bang 18: Cac pirazolin chua hgp phan cumarin (Pf,.,)

Haiij^ 10; Kli;i iiAiij; kh;uig khuan \ a 1. liOnji nam cim c:\c x c l o n (X, p- khAng no day

hidroquinon va resoxinol

Bang 20: Kha nang khang khuan va cho'ng nam cua cac xeton a. P- khong no day cumarin

Bang 21: Kha nang khdng khuAii vu chong nam cua cac [)ira/olin day cuiiiarin

DANH MUC CAC HINH

Hinh 1: Phd cong huang ti^ proton cua san phiim chuyen vi Fries 8- axetyl- 7- hidroxi-

4-inetylcumarin.

Ffinh 2: Phd khoi lugng cua san pham chuyen vj Fries 8- axetyl- 7- hidroxi-

4-metylcumarin.

Ffinh 3: Phd cOng huong tu prolon cija xeton a, P- khong no CL

Hinh 4: Phd kho'i lugng cua xeton a, P- khong no Cl.

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IVi-A T NHUNG KEI QUIVi-A CHINH

D6 tai: "Nghien ciiru tdng hgp, caiu true va lioiit tinh sinh hoc ciia cac ligp chai tuong lu

Flavon, co chiira nlian cij von^"

Chinh thirc dugc phe duyet la de tai dac biet cap Dai hgc Qudc gia Ha ngi vao Ihdng 05 nam

2001. vdi thdi han 24 thdng (ke tu ngay kf) va ldng kinh phi 60 trieu dAng. Den nay, de lai

da dugc lumn lhanh va dai dugi ci\c kei ipid chinh nhu sau:

1. Ke't qua ve mat khoa hoc:

Da nghien cihi phan ung chuyen vi Fries cdc aryl axetat di tu ddn xuat cua quinolin,

Ogicnol vii isoogicnol, cdc dihidroxibcn/cn, cdc hidroxi ciia cumarin va quinolon- 2. San

phdm cua phan ihig nay la cdc chdt ddu cho cac chuyen hod licp theo.

Da thuc hien phan ung ngung tu giua cac san pham chuyen vi Fries a tren v6i cac

indol - 3 - andehit hodc v6i cdc andehit day Furan lrong dieu kiCn ciia phan ihig

Claisen-Smith d^ nhan dugc cac day xeton rx, p - khAng no luong ung co chira cdc nhan di vong

(khoang 50 hgp chat mdi).

Ti^ cdc hgp chai xclon (/., \\ - khAng no nhan dugc d Iren da cho phan ung cAng hop

vong oxi hod boi lim huynh de lao thanh khoang 40 hgp chai mdi tuong lu Flavon nhung

chua nhan di vong hoac cho ngung lu ddng vong vdi phenylhydrazin de lao thanh khoang 50

hop chai niiVi ciia vdng pira/olin.

Cau true cua cac iigp chdl mdi nhan dxsac da dugc xac nhan nhd cac phuong phap phd

hdng ngoai, tir ngoai. phd cAng hmmg lir hat nhdn va phd khdi lugng.

Da van dung cdc plurctng phdp ti'nh Hod lugng lir ti'nh gan dung dc xdc djnh mat dd

dien tfch Iren cac vi Iri lrong phan tir. xac dinh do dai va nang lugng lien ke't trong phan tir.

Tren CO sd do da xdc dinh cau h'mh uu tien ciia phAn tif, ddng thdi gdp phdn lam sang ro

them ve chieu hudng va co che phan i'mg.

Da tham dd hoat tfnh smh

IIDL

ciia mgl .so Ja\ chat tdng hgp dugc va xdc djnh dugc

khoang 30 hgp chat cd hoat tinh khang khuan vii chdng nam d muc do khac nhau. trong dd

cd mot sd chat rat dang chii y va cdn dugc nghien cirii sau hon.

Vdi ke'l qua do da cAng bd cdc cong trinh sau dav:

1. Nguyen Minh Thao, Nguyen Oinh Dong,

^Tdng hap vd chuyen hod mat sd xeton a, P- kliong no co chim vong indol vd quinolin \

Tap chi Hod hoc. T.3^). so 2, Tr. f^O (2001)

2. Nguyen Minh Ihao, Fhani Van Phong,

'Tong hap vd chuyen hod cdc hap chdt tuang tu khan con cd chda vong indndTi. T6t^

hap vd chuyen hod cdc hap chat xeton a, p- khdny, no tif cdc 3-fom\lin£n w J^ tuai

agienol \

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veton ce, fi- khong no tii ddn xudt cua isoagienol vd cdc

indol -3- andehit \

Tuyen tap cdc cdng trinh klioa hpc ki niem 45 ndm ngdy thdnh lap Khoa Hod hpc (1956

-lOQIh Nhd xudt hdn "DHQGHN" - Hd Noi - 2001, tr. 52-55.

4. Nguyen Minh Thao, Pham Vdn Phong.

'Xdc dinh cdu hinh cua agienyl axetat vd sdn phdm chuyen vi Fries cua nd bdng phuang

phdp tinh Hod luang tu\

Tap chi Hod hpc, T.40, so J, tr. 9 (2002)

5. Nguyen Minh Thao, Pham Vdn Phong,

*Xdc dinh cdu hinh cua xeton a, /?- khdng no (td o -axetylagienol vd 3-fomylindol) vd mot

vdi sdn phdm chuyin hod cua nd hdng phuang phdp tinh todn Hod luang td\

Tap chi Hod hpc, T.40, so 2, tr. I-10 (2002)

6. Nguyen Minh I hao, Nguyen Van Ndm, l*ham Van Phong,

*Tdng hap vd chuyen hod mat sd xeton a, fi- khdng no ta axit dehidroaxetic vd cdc

furfural\

Tap chi Hod hoc, T.40, so 3, tr.43 (2002)

7. Nguyen Minh Thai), Pham Vs^n Phong, Biii Manh Tung, Phi Thi Minh Hai,

'Tong hap vd chuyen hod mot sd xeton a, fi khdng no di tut ddn xudt cua Hidroquinon vd

cdc indol- 3- andehit \

Tap chi Hod hoc, T.41. so I. tr. 6/ (200.^

H. Nguyen Minh Thao, Pham Van Phong,

'The quantum calculating application in Fries rearrangement of resorcinol diacetate \

Bdo cdo lai Hdi nghi Khoa hoc Chdu A lan tht'r 10 hop tai lid noi vdo ngdy 21- 24 thdng 10

ndm 2003.

9. Nguyen Minh Thao, Pham Van Phong, Nguyen Xuan Tu,

\Synthesis and transformation of some ac, fi unsaturated ketones from coumarine

derivatives and indole- 3- aldehydes \

Bdo cdo tai Hoi nghi Klioa hoc Au- A Idn thif VIII hop tai Hd noi vdo ngdy 21- 24 thdng 10

ndm 2003.

2. Ket qua phuc vu thuc tc:

Viec tham dd va xac dinh dugc mot loat hgp chat c6 kha nang khang khu an va chdng

nahi da la su dinh hudng ung dung thuc le. Hien nay mot vai hgp chat dang chii y dang dugc

tie'n hanh thir hoat tinh chdng ung thu va cd the ca chdng HIV. Ne'u cd ket qua tdt thi dd se

la cu ddng gdp tdt cho phuc vu thuc tc.

Ngoai ra. ke't qua dao tao ve mat nao do cung cd the coi nhu la kel qua phuc vu thuc

te.

3. Ket qua dao tao:

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Ig) Ngoai ra ci>n I hgc vien cao hgc khac da hoan t h ^ h

chuong trinh hgc tap nhimg chua bao ve luAn van.

- Da hudng ddn 08 sinh vien bao ve thanh cAng khoa luan lAt nghiep: Trdn Van

Chie'n. Nguyen Manh Cudng, Nguyen Van Nam. Bui Manh Tung, Hoang Hie Thdng.

Duong Thi Hd. Rii Thi Minh Hai. Le Thanh Nghi.

- Da hudng d ^ mdt sd sinh vien lam nghien cuu khoa hgc lhu dugc ket qua tdt, Irong

66 cd sinh vien Nguyen XuAn Tir dat ket qua rat tot, dat giai nhi NCKH ciia sinh vien

Trudng DHKHTN va giai khuye'n khfch nghien cmi Khoa hgc Sinh vien cdp Dai hgc Qudc

gia Ha ndi nam 2003.

4. Ket qua ndng cao tiem lire khoa hoc:

Tren CO sd Ihuc hien de tai. da dao lao mol <6 thac si va cu nlmn. trong dd co nhi^u

ngudi trd thanh can bA cd nang luc. MAl sd sinh vicn sau khi bao vc khoa iuAn tot nghiCp da

dugc de nghj chuy^i tie'p cao hoc nhu Phf Thi Minh Hai. Ilianh viCn de lai Fliam V.ln Phong

sau khi bao ve xua't siic luan vdn thac sT cung dii heu chuan de dugc xet chuye'n tie'p nghien

cun sinh.

Ve mat thi6^t bi, nhd viec thuc hien de tai vdi ngudn kinh phi dugc cdp ciing da tang

cudng mdt sd dung cu cdn thiet cho qua trinh thf nghiem nhu lii dd, bep dien, cac dung cu

ihuy linh di^c biei. va dac biei cd ngudn kinh phf dd mua cdc loai hod chdt dac biet phuc vu

qud trinh nghien ci'm.

5. Tmh hinh stir dung kinh phi:

Tdng kinh phi dugc cdp cho 2 nam Ihirc liiCn dc tai la 60 trieu ddng (niAi nam 30 trieu

ddng). Kinh phi chu ye'u dugc diing dc mua hod chat va dung cu thf nghiem . Mot phdn chu

yeu khac disac dung de thue mudn chuyen mdn va lao dong. De'n nay da quyet loan dugc

khoang 52 IriCii. Cdn hu khoang S Iricu sc dugc qiiycl (odii ngay sau khi nghiem thu de lai.

Hd noi. ngdy i^'thdng tenant 2003

XAC NHAN CUA TRUONC; OAI HOC

TUNHIEN. DHQC.HN

OHO MIEL T R J O N O ^^' '

( IIUNIIlftMDft IAI

.'C'^ffhi Jfrj/fU GS. TSKH. Nguyin Minh Tndo

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e and biological activity of the analogs offlavone

compounds containing heterocyclic nucleus'*

ABSTRACT

The Fries rearrangement reactions of aryl acetates from derivatives of quinoline. eugcnole,

isoeugenole, dihydroxybcnzenes, hydroxyquinoloncs, hydroxycoumarincs have been

studied. These products have been used as starting reagents for conscqucnl lransii>rmalit)ns.

Tlicn, the Fries rearrangement producls have been condensed in the conditions of

Claisen-Schmidt reaction with indole- 3- andehydes or furfuraldehydes to give a, P- unsaturated

ketones containing heterocyclic nucleus ( about .50 new compounds).

The a, p- unsaturated ketones were cyclo-aditionaly transformed by Sulfur as an oxidizing

reagent, forming about 40 new flavone analogs containing heterocyclic nucleus. The a .

P-unsaturated ketones also easily reacted with phenylhydrazine to form about 50 new

derivatives of pirazoline ring.

The constitutions of the producls have been determined by using IR-, UV-, MS- and

'H-NMR- spectroscopies, and the their antibiotic abilities have also been tested. Some of them

have shown good results and wc have been proposed to enlarge the research in order to

dclerminc and developc the resulls.

Besides synthetic reactions. Chemical Softwares, such as HypcrCiicm 7.0. have also been

used lo help determining charge density, binding length, and binding energy of molecularly

optimal confonnations and studying mechanisms of the reactions.

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>an phim thu dugc bang cdc phuong phap pho hien dai :

hdng ngoai, tir ngoai, cong hudng tir proton va khdi lugng... cung nhu sir dung cac phuong

phap tinh hoa lugng tir gdn dung de xdc dinh mdi d<} dicn tfch, dA dai va nang luong lien k^t.

cQng nhu cdc cdu hinh ben ciia phan tir. Tir dd cd the gdp phdn lam sang ro them chieu

hudng va co ch^ phan ung.

- Ti^n hanh tham dd hoat tfnh khang khudn, chdng ndm va xay duu^ Inrdc ddu mdi

quan he giGa cdu tnic phdn tir vdi hoat linh sinh hgc ciia hgp chat ldng hgj) dugc.

De thuc hien 66 tai. chiing ldi da sir dung cac phuong phdp thuc nghiem lien lien

trong tdng hgp huu co, cac phuang phap phd hien dai va phuong phdp tinh gan dting cua hoa

lugng tir de xem xet cdu tnic phan tir va phucrng phap tham dd hoat Ifnh sinh hgc theo lieu

c h u ^ trong dugc dien Viet nam.

n . TONG QUAN CAC VAN

D £ N ( ; H I E N

CUU:

2.1. Ve phdn Umg chuyen vi Fries:^^-'^' ^' '

Phan ling chuyen vj Fries la qud trinh chuyen \'i ngi phdn tir ciia cac phenyl este nhd

su xiic lac ciia axil Lewis (AlCl^, ZnCl2, BF^...). Phan ung xay ra vd ban chat gidng vdi su

the'electrophin (Sg). Thf du:

OCOR OH OH

AK.h

COR

Co che'chung ciia phan ung dugc trinh bay Irong so dd sau:

'OAlt'h

» KC c>

-COR

o i l

O ^ R 
/?-axy^>hL'nr)l

A l ( t ,
li

( I

a.\ylplfc;ni)l

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2, dieu kien cd dung mdi vkhi este d Ihe ran va cd nhiet

dd ndng chay cao) hodc khong cdn dung mdi. Ca»; dung moi thdng dung !a liilrobenzen,

caebon disunfua hodc diclocian... Iiong dd liiii'ihcn/m (d mi liie fi*ni' a vt no \ir:i hoa tan

nliAm clorua khan, viTa hoa tan este.

2.2. Vi cdc xeton a; fi khdng no:

2.2.1. Cdu fuocac xolon a, \\- khong no:

Cdc xeton a, p- khAng no Id cdc hgp chdl hihi at ma trong phan lir ciia chiing cd chira

nhdm vinyl xeton (-CH=CH-CO-). Chi'nh vl vdy ma cdc xeton a, P- khdng no cd kha ndng

tham gia nhi^u phan ling dd lao thanh cdc hgp chdt hiru co khdc nhau.

Plid hdng ngoai cua xeton a, p- khAng no thudng xudt hien cdc pic ddc liimg cho dao

dOng hda trj cua nhdm C = 0 lien hgp trong klioang 1630- 1690cm'. ciia ndi ddi lien hop

ciing vdi cac ndi ddi cua vdng thom lrong khoang 1550- 16I5rw"' va pic dac tnmg cho dao

ddng bi^n dang khdng phang ciia nhdm trans- vinyl d 960- 990c7« ' ''*'

Hid lir ngoai ciia cdc xclon <x, \\- khdng no Ihuirng cd 3- 4 cue dai ha'p lhu ndm d viing

tir 300«w trd len vdi he sd tdt phdn tir khoang lO'^ dac Irung cho budc chuyen electron

n->7r*. 240- 290nm vdi he sd Idt phdn fir khoang 10^ dac Irung cho su chuyen budc chuydn

electron n->n* va 200- 2?iOnm dac Inmg cho su chuyen budc chuyen electron K—>7i* cua

nlian benzen''*''.

Ngoai ra cdn cd cdc cue dai vdi ^,„;„ nhd hon dac trung cho nhan thom, di vdng....

2.2.2. Cdc phuong phap tdng hgp xeton a, P- khdng no:

Cac xeton a. P- khdng no cd ihd dugc ldng hgp bang nhidu phuong phdp khac nhau.

chdng han lx\ng phan ihig ngimg tu ciia ankyltriphenyl photphoclorua vdi andehit piruvic'''.

bang su quang ddng phdn hda 4- (benzanamino)- 3- melyl- 5- sliryloxazol'"', bdng su phan

huy cdc p- aminoxeton''^-'" '", bdng each loai phan tir nudc ciia diaxetoancol''^' va dac biet

bang phan ung ngung tu Claisen- Schmidt"^':

*^0-<N O OH O

^+'1^-'^ H"(HO") M I - H7O II

AAC-CH3 + R~CHO 5 U - A r - C - C H 2 CF*-R ^ • A r - C - C H = : C H - R

I II

lluin ung cd ihc dugc f.huc hiCn vdi xiic tac axil hoac h•<^z^1, nhung thudng xiic tac

bazo cho ket qua lot hon. Co the ndi ddy ia phumig phdp phd bien nhat dd tdng hgp cac

xeton a, P- khdng no.

2.2.3. Tmh chat ciia cac xeton a, fi- khdng no:

Cac xelon a. p- khdng no cd the Iham ;^ia ra<; pluin \sv\)j. a i\-)i doi ;ieng biet (cAng

bn>m hay oxi hod bdi KMnO,) hojc phdn (m,u tivit nhdm CO iihi du lao ra

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di ca he xelon a, p- khAng no lien hgp de lao thanh cac

dJn xuit cua vong pirazolin hoac isoxazolin...

Thfdu"^':

o

KCftll., C CM C M — t \ . i i , i r

r,,HsNiiNn>M( n i . o

R'\UCu

N

I

2.3. Vdi net ve flavon vd flavonoit:

Flavonoit ndi rieng va flavonoit ndi chung la mgl nlidrn hop chdl rat rdng Idn va

phong phii lrong nhien thuc vdi. Chiing cd the d dang tu do hodc dang glycozil.

Chung cd Ihe dugc tdng hgp bang nhidu phuofng phap khac nhau. (Jhiing han:

Tdng hgp theo Koslaneski- Robinson" *':

C O C H

O i l

{Co\hCOhO/i'tM,0

Q

CO( II

o ( r)( f.Ms

M.O

Cf^lh

Tif o- axelylphenol va cdc csli

COCMj

Cf.tlsCfX'l
»>
Pirklin

I 4 | .

( ( K M

KOII

OH - " \ / OC(X ftlls

Tit o- axelylphenol va andehit Ihom"'* '"^

o

COCHj

KOII 60%
+ CftHsCIIO

»-Pirtdin

C M(( (K)ll
MjSO^

( r Cf,Us

OM C>llsOM

M.

O^ "CftH5

(NaHCỘ 20**C)
O

(C,.H5)3C*CI04
(CMiCO),0

^ o - -c:,,H5

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U VA T H U C N G H l f e M :

3.L Phuang phdp xdc dinh cdu tao dp tinh khiet vd hoat tinh sinh hpc cua cdc hap

chdi tong hap duac:

- Sdc kl lop mdng dugc thuc hien tren ban mdng trdng silicagel. He dung mdi etyl

axetat: clorofom = 1 : 4 . Hien hinh bang hoi idt hoac d\ia\ dnh sdng tir ngoai.

- Phd hdng ngoai dvxoc ghi dudi dang cp vien vdi KBr tren may P I - IK 1801 Shimadzu

tai vien Khoa hgc Hinh su- Bg cong an, Trung ldm Hod inAi trudng va phat tricn bdn vung,

may Nicolet 760 E. S. P. Trung tdm Hod dau, mdy Nicolet Avatar 360 Sl - IR eP ciia phdng

thi nghiem VH-I Trudng Dai hgc Khoa hgc tu nhien- Dai hgc Qudc gia Ha ndi.

- Phd tu ngoai ciia cac hgp chdt dugc ghi Iren may Spectrophotometer UV- 2001 trong

dung mdi etanol tai Phdng may- Bg mon Hod Vo co- Khoa Hod hgc- Trudng Dai hgc Khoa

ligc lu nhien- Dai hgc QuAc gia Ha noi .

- Phd cAng hudng tir proton cua cac hgp chdt dugc ghi Iren may BRUKER AVANCE 500

MHz trong dung mAi DMSO- d^, vdi chdt ndi chuan IMS tai phdng Hod cdu true Trung tarn

Khoa hgc Tu nhien va CAng nghe Qudc gia.

- Phd khdi lugng ciia cdc h(;p chdt dmc ghi tren may 5989 BMS tai phdng hoa cdu tnic

Trung tam Khoa hgc Tu nhien va Cong nghe Qudc gia.

~ niir lu)al Ifnh khang khuan \l\ chdng nam diroc Ihuc hicn lhc(^ phuiyng phdp ghi trong

dugc die'n Viet nam (Idp kluiiig sinh dC)) tai Phdng ihi nghiem Hoa sinh XMzuh \ ien 19-8 B(>

cdng an va lai Medilalec Co. Ltd (38 Chau Long- Ha ngi).

3.2. Tdng hap cdc este cda phenol vd thuc hien phdn iaig chuyen vi Fries cua chiing:

3.2.J. Tdng h(/p cac aryl axetat WsXa cda cac phenol):

Dun si\\ hdn hgp phciu>I \d\ juhldiil ;i\clit. (ti Ic mol 1:1 \ai monophcnol vd 1:2 vdi

dihidroxiaren) vdi sued mat ciia Iml a\il photpiioric dac ldm xiic tac lrong sudt 3- 5 gid. Cai

loai axil axetic tao ra lrong phan ung va anhidrit a:<ctic du. Tach lay Idp huu ca, rira bang

dung dich NaOH loiing rdi nra lai nhieu Idn bdng nuoc. lam khd rdi cat lay cstc d dp sudt

thdp (trong trudng hgp cd dung mdi de chicl thi trudc khi cat Idy este phai cdt loai dung nidi

trudc).

Vdi cac dihidroxibcn/cn thuinig chi diing axil sunfuric dixc h\m xiic lacva chi cdn

khuay trdn hon hgp plu'ui iuv^^ d nhiel dd phdng sO (hu dugc cstc thudng d trang thai rdn.

Dudi day la cdc este khdi ddu tdng hgp: duac:

- Qgienyl axetat: t", 163- l67"C/23minHgi"'. Hieu suat 53%.

- MYM/gicnyl axelal: I',„ 78- 8(r'C. Hieu sudi Ky/v.

- Resoxinyl diaxelal; i'\ 278"C (Theo lai lieu ' " ' . I'; 278"C). Hieu sudt 70%.

- Hidr(K|uinyl diaxelal: t"„. I22'C (Theo lai lieu ' " ' . t',„ I22'C). Hieu sudt 84%.

</div>
(13)<div class='page_container' data-page=13>

Icumarin: C,., 150- 15r'(: n i i c o lai lieu " " ' . t",,

L50-I51"C). Hieu sudt 90%.

• 8- Quinolinyl axetat: C,, 56- 57'C

(TIKM.

lai lieu ''"'. i".,. 56- 57C). Hien sudt 60%.

3-2.2. Thuc hien phan utig chuyen vj Frits este cua cac phenol:

Dun ndng hdn hop este ciia phenol vdi AICL khan Ihco li le mol I: 2 hay I: 3 luy theo

este hodc diesie (cd Ihe' khong dung dung moi hoac dimg dung mAi iiitiol)en/eu) d

170-180"C sudt 3 gid. Sau dd phan huy hdn hgp bang nudc da va axil clohidric dac. San ph^m d

dang ke't tinh dugc lgc hiit. rira vu lam khd ngoai khAng khf (in)ng trudng hgp dimg

nitrobenzen lam dung mdi thi phai cdl loai nitrobenzen bdng chung cdt Idi cudn hoi nudc).

Cac san ph£m phan ung chuyen vi Fries duac ghi trong bang I.

Bdng I: Cdc sdn phdm phdn ifng chuyen vi Fries

^

Phenol khdi

dSu

San pham chuydn vi

urc)

Hieu suat

(%)

Phd hong ngoai (cm ^)

'on

agienol

oil

II^CO^ J^ ^((K II,

100-102

50

C I U H-Clh

3442

1603

Isoogienol

on

H3CO. J \ /COCMj

179-180

( II CIKII

Resoxinol

1^6- UJ

COCH^

Resoxinol

Hidroquinon

CH.CO

OM

84-85

110 / r ^ \ COill

202- 203 74

31

60

64 3366

1615

3200

3248

1620

1630

1640

</div>
(14)<div class='page_container' data-page=14>

7

methylcumarin

8-hidroxiquinolin

COC

.<^^^^^^

(

111 ^o-^o

^H^^^^COCU,

OH

162-163

' 8 2 - 8 3

73

75

3370 1632

*: Hid 'IK NMU,d/vw/: ..'.53 {(\\d\ (^.?^(>i\\ <' ): <>^^ (I I ( \ ) : 7,72 (IL i\,)

==: I^d 'H- NMR. bppm: 2,53 va 2.73 (2CTL); 6.48 (ll-C\); 8,(K) (H- C,)

***: Phd 'H- NMR, hppnr. 2,6()(CH,); 6,80 (H-C.); 7,00 (H-C,); 7,20 (H- C ) ; 9,20

(HO-CV 11.30 (HO-C,).

MS: I52(M*); 137 (KK)';;-) (M'- CH,); 109 (M' (II.CO).

****: Phd 'H- NMR, bppm: 2,40(CH,); 2,60(CH,C()); 6,20 C,): 6,90 C,); 7.70

(H-C,); 11.30 ( H O - C J .

MS: 218(M); 203(UX)%) (M' - CH,); 190 (M - CO).

3.3. Fhuang phdp chung tdng hap cdc xeton a, /A khdng no:

a. Trong su lam lanh ben ngoai bang nuc'jfc dd, khuay trdn hdn hgp ddng tl le mol ciia

cdc hop chdt kieu o- hidroxiaxclophciioii (c;ic s;in phiim chuyen vi Fries- Bang I) vdi cdc

andehit day indol hoac furan lrong etanol vd cd mat xiic tac la dung dich NaOH 30- 60%.

Sau dd de yen hdn hgp phan ung d nhict do phdng 120 gid. Tie'p theo pha loang hdn hgp

phan ling bang nU('/c dd de'n gdp doi the tfch ban dau rdi trung hoa bdng lugng axit axetic

dugc linh sdn den phan ung trung tfnh. Lgc hut ket tiia tdch ra, dc khd ngoai khong khf va

cd the ket tinh lai tijrdung dich etanol- nudc.

h. D6i vdi cac hgp chat la axil dehidio axclic hay axctylcumarin thi thuc hien phan

i'rng bdng each dun ndng hdn h(;p ddng li lc mol ciia hai chdt phan ung lrong clorofom vdi

vai gigt piperidin lam xiic lac lrong sudt 3- 5 gid. San phdm o dang ket tiia dugc tach ra

bang lgc hiit va do khd ngoai khdng kin'.

Ke't qua dugc gidi thieu d cac hang 2. 3. 4, 5. 6. vd 7.

</div>
(15)<div class='page_container' data-page=15></div>
(16)<div class='page_container' data-page=16>

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</div>
(19)<div class='page_container' data-page=19>

3,4. Phuang phdp chung long hap cdc hap chdt tuang tu flavon:

Dun sAi hdn hgp theo ll le mol i: I cua xclon (x, |1- khAng no vdi luu huynh trong

xilen sudt 6- 8 gid. San phim tach ra d dang linh Ihe dugc Igc hiit va de khA ngoai khdng

kill. ( O diO'' kci linh lui lir dtiiif; ilii h rlaiiol: tiuac

K6i qua dugc gidi thieu trong cac bang 8, 9, 10, 11, 12.

/?a/ig 8: Cdc hap chdt tuang tu flavon di tit agienol vd isoagienol (Fp,^)

TT.
FEI 
Fs2

Fn

F^

Fes 
F^

xeton a ,
p-khongno
l£1
E2
E3
E4
E5
F6

1

U'^)

200-202
198-200

224-226
194-196
73-75
189-191
Rf
0.60
0,35
0.54
0.55
0.36
0.54

, 1

Hi6u
suat

(%)

IX) 
85
80
60
48
40
%N
Tinh
4.23
4.06
3,44
3.33

-Tim

4.38
4.34
3.72
3.57

-'

Phd h(V)g ngoai (cm')

V c ^

1632
1629
1624
1658
1645
1615
vcoc
1130; 1240
1245
1174.1247
1175.1260
1043; 1265
1037; 1267
Phd tGrngoa
KJnm)(}QE)

241(4.19); 257(4.10); -; 294(4,42)
243(4.45); 264(4.51); -; 301(4,54)

-; 255(4.71);-; 312(4.41)
244(4.40);-;-; 298(4.43)

-n

F„,

FR,
FR,
FR,
FR,
'Dttti
ã"DRZ
'DWJ
|Fnô,
xclon
Rl
R2
R3
R4
R5
l)1W
DR7
DR8
DR9

Bdng ^>

wrc)

193-194
203-204
255-256
150-151

105-106
20!> ?0(J
21S-216
161-162
242-243

'; Cdc hap elicit tuang tu

R,
1.54
0.70
0.45
0.63
0.48
O.Mi
0.73
0,52
0.50
Hi6u
sunt

(%)

64
75
50
65
52
wi
78
69
67

%N
Tinh
5.05
4.81
3.97
4.81
3.81
r»..u)
5,93
5.93

-Tim
5.25
4.78
3.83
4.95
3.54
Ei.)2
6.12
6,10

-flavon

di tit resoxinol (FRJ.S vd Fpufi. 9)

Phd hong ngoai (cm')

v « i

3169
3165

3137
3245
3136

-^'c-fl
1637
1633
1629
1643
1623
m.\r 
1615
1693
1628
Vcor
1128:1214
1084; 1263
1085; 1244
1170; 1257
1084; 1243
\\yf. VM 
1161; 1243
1125; 1210
1175; 1245

Phd tiJr ngoai
X^(nm) (tge)

210(3.71); 250(3.46); -; 407(3.60)
-; 256(3.90); 364(3.68)
204(3.94); 245(3.71); 266(3.59);

302(3.55)

2(Xi(3.64); -, 258(3,37); 362(3.62)

?2:'H3.75). 253(3.39). 412(3.58)

210(3.83); 240(3,75); 263(3,56);
314(3.65)

</div>
(20)<div class='page_container' data-page=20>

F,„

F„2

F.n

F,M
F,.s

xeton

HI
H2
H3
H4
H5

bane W: L

UfC)

178-179
19&-199
230-231
152-153
192-193
R.
0.52
0.53
0.56
0.61
0.63

ac hap

Hieu
suai
(%)
65
75
71
64
70

Chdt tuang tu flavon di tit hidroquinon (F^.^)

%N
Tfoh
5.05
4.81
3,97
4.81
3.81

Tim
5.21
4.91
3.75
4.88
3.60

Phd h6ng ngoai (on')
V a .

3167

3245

3200
3259

3248

V c o 
1644
1634
1618
1635
1642
Vcoc 
1132; 1217
1162; 1218
1176; 1241
1137; 1211

1135; 1216
Phd tungoai
X ^ ( w n ) ( t g f : )

222(4.38); 257(4;25); 287(4.18);
412(4.41)

210(4.75); 2*^5(4.36); 266(4.15);
303(4.28)

-208(4.76); 259(4.54); 303(4.16);
364(4,12)

-Bdnn 11: Cdc hap chat luang tu flavon di tir hidroxiquinolin

(FQI,^)

TT
Fo,
Fo,
Fo,
xeton
Ql
Q2
Q3
04

wrc)

191-192

180-181
251 252
102-103
R.
0,49
0.43
0.42
0.46
Hieu
s u ^

{%)
7a,
80
69
72
%N
hnt)
8.9
8.6
7.2
6.9
Tim
9.1
8.2

/.o

7.1

Phd hdng ngoai (cm^)

V . i ,

1634
1635
1621
1661
Vux; 
1124;1242
1160.124?
1 U 5 . 1245
1174;1244

V M I

3167
3266
3128

-Ptid turngoai
X ^ ( n m ) ( l 9 E )

241(4.58); 256(4.48); 294(3.94)
241(4.46); 263(4.31); 300(4.45)

-; 256(4.62); 312(4.35)
242(4.48);-; 298(4,40)

Bdng 12: Cdc hap chdt titang tu flavon di tir axit dehidroaxetic (Ff),f^ ,.12)

TT.
*lH4t 
^BHA2 
^0HA3 
FoHA4 
FBHAS 
FBHAS 
1 ^BNA7 
'^OHAM 
FBHAS 
'DHA1$ 
'BHAIt 
*BHAt2 
_

1 Xeton

D H A l
DHA2
DHA3
\)\\M 
DHA5
DHA6
DHA7
0 H A 8
DHA9
DHA10
DHA11
DHA12

1 urc)

258-260
208-210
212-m 
2/4-2/5
207-209
215-216
247-248
259-260
185-186
173-174
119-120
158-159

1 ^

0,40
0.47
0,56
0 . 4 /
0.54
0.42
0.5C
0.57
0,59
0.44
0.35
0.65
HI6u
(%)
73
75
55

83
92
71
P^
C3
78
69
GO
47
%N
rmh
4.81

nm

5.03
4 . M j 4.31
3.81
4.59
3.67

-3.a3

---•
4.19
4.32
4.01

-Pttd tiong rejoai ( c m ' )

V c o

1695; 162a
1695; 1528
1716; 1647
1714.1041
1713; irvt?
1722.1060
1718. 1540
3,97

-4.81 1 4.65

• 1

-1720:1660
1685; 1666
1728; 1640
1718; 1641
1719-154((
Vcoc 
1244
1244
1224
1180
1242
1263
1249
1253
1233

1245
1252
1253

Phd I I ; ngoai
> _ ( « m ) ( t g , : )

221(4.?^). 263(4.64); 284(3.76); 432(4,33)
210(4.56); 244(4^:5); 302(4.21). 452{?,53)

-; 239(4.33): 3 0 : (4.19); 446(4,40)
22/(<.12): 28'l{:i.r)9), ;-;i6(3.62); 431(4.46)
22/(4.27). 235(3.73): 32a(3.G9); 432(4.42)

2 0 9 : 2 4 1 ; - ; 383
209; 255; -; 381
209;251;35G;;«'.9

210; 23a. 3 1 7 ;
-201; 2 4 8 ; - ; 393
2 0 1 . 2 2 5 : 3 0 8 : 3 6 4

201; 2 3 1 ; - ; 356

</div>
(21)<div class='page_container' data-page=21>

J.J. rnuangpnap chung tdng hgp cac pirazolin chua nhdn di vdng:

Dun sAi h6i luu hAn hgp theo ti le mol I: 1 ctia xclon r/, p- khong no v(5ri

phenylhidrazin trong etanol vi su c6 mat vai gigt axil axetic liim xiic tac suAt 3- 5 gi5. San

pliiim tach ra (V dang ke't tua dugc Igc hut va de khA ngo^i khAng khi.

K^t qua dugc gidri thieu 6 cdc bang 13, 14, 15, 16, 17 va 18.

Bdnz 13: Cdc pirazolin chita hgp phdn agienol vd isoagienol (PEL 6)

TT.
PE.
P D
PE3
Pw
P..
PE«
Xeton
E l
E2
E3
E4
E5
E6
ticTC)
158-160
166-168
138-140
114-116
177-179
107-109
R,
0.71
0.65
0.83
0,77

0.56
0,53
Ht^suat
(%)
74
61
55
75
78
72
%N
Tnh
9.93
9.61
8,42
8.22

-Tim
9,64
9,33
8.25
8.50
^

-Phd hdng ngoai
Vc^cm')
3358
3378

3395
3296
3385
3285

Phd tur ngoai: A^(nrn) (Ige)

225(4.45); 305(4.41); 341(4.55)
224(4.19); 266(4.10); 300(4,07)

-; 254(4.36): 306(4.09)
-; 302(4.32); 341(4.52)
205(4.17); 225(4.28); 250.280.

305(vai); 340(4.77)
202; 225(4,64); 235; 283;

305(vai); 340(394)

Ddng 14: Cdc pirazolin chda hgp phdn resoxinol (Pjf,,^ vd PoRf,.9)

TT.
PRI
P.ô
Pm
Pw
PRS
PDô
ã tô7 
Ptôl

PDTS

xeton

R l
R2
R3
R4
R5
DR6
DR7
DR8
DR9
W(°C)
173-174
144-145
237-238
170-171
139-140
165-166
199-200
277-278
171-172
Rf
0,56
0.67
0.74
0.71
0.78
0.57
0.62
0.66

0,75
Hi6usuat
(%)
74
72
51
46
60
65
73
40

1

''

1

%N
TWi
11.38
10.97
9.44
10.97
9,15
13.38
12.80

-12,80
Tim
11.10
10.85
9,30

11,17
9.33
13.12
12.50

-1^50

Phd hdng ngoai
V ^ J o n ' )
3432. 3381
3118,3380
3150.3138
3311
4448.3312
3400.3388
3417. 3379
3448
3448

Phd ttf ngoai:

^™.('wn)Ogi:)
220(3,85);-; 338(3.56)
225(3,55); -; 344(3.67)

-250(4.05);-; 340(4.21)
230(3.69); 291P.36); 337(3,52)

230(3,66); 266(3.24); 346(3.33)

-223(3,48); 291(3,11); 365(3.15)

</div>
(22)<div class='page_container' data-page=22>

J.J. rnuungpnap cnung long nap cac pirazolin chua nhdn di vong:

Dun sAi h6i luu hAn hgp theo (i le mol 1: 1 ciia xeton a, ^~ khong no voi

phenylhidrazin trong etanol \h. su co mat vai gigt axil axetic lim xiic lac suol 3- 5 gicr. San

pliiim tdch ra (V dang ke't tua dugc Igc hiit va de khA ngoii khAng khi.

K^t qua dugc gidri thieu 6 cac bang 13, 14, 15, 16, 17 va 18.

Bdne 13: Cdc pirazolin chiia hgp phdn agienol vd isoagienol

(PEI.6)

TT.
PE.
P K
P B
PB4
P.^
PE«
Xeton
E l
E2
E3
E4
E5
E6

wrc)

158-160
166-168
138-140
114-116
177-179
107-109
R,
0.71
0.65
0.83
0.77
0.56
0.53
Hteusu^

(%)

74
61
55
75
78
72
%N
Tffih
9.93
9.61
8,42
8,22

-Tim
9.64
9.33
8.25
8,50

-Phd hdng ngoai
Vc^cm')
3358
3378
3395
3296
3385
3285

Phd lu ngoai: Kmknm) (Ige)

225(4,45); 305(4.41); 341(4.55)
224(4.19); 266(4.10); 300(4,07)

-; 254(4,36): 306(4.09)
-; 302(4.32); 341(4.52)
205(4,17); 225(4,28); 250.280,

305(vai); 340(4,77)
202; 225(4.64); 235; 283;

305(vai); 340(394)

Bdng 14: Cdc pirazolin chda hgp phdn resoxinol (Pf^,,^ vd

PDR^-V)

TT.
PR.
P.U
PR3
PR*
P«.
Ptw
"vm 
PpB.

1 Pora

xelon

R l
R2
R3
R4
R5
DR6
DR7
DR8
[)R9
tncTC)
173-174
144-145
237-238
170-171
139-140
165-166
199-200

277-278
171-172
R,
0.56
0.67
0.74
0.71
0.78
0.57
0.62
0.66
0,75
Hi6usuat

(*)

74
72
51
46
60
65
73
40

''

1

%N
Vnt\ 
11.38
10.97
9,44

10.97
9.15
13.38
12.80

-Tim
11.10
10.85
9.30
11.17
9.33
13.12
1Z50

-12,80 12.50

Phd hdng ngoai
V.„{rm')
3432. 3381
3418,3380
3150,3138
3311
4448.3312
3400.3388
3417. 3379
3448
3448

1 Phd hjr ngoai:

A„Jnm)(Igc)
220(3.85);-; 338(3.56)
225(3.55); -; 344(3.67)

-250(4.05);-: 340(4.21)
230(3.69). 291P.36); 337P.52)
230(3.66); 266(3.24); 346(3.33)

-223(3.48); 291(3,11); 365(3.15)

</div>
(23)<div class='page_container' data-page=23>

n.

PH,
P«
PH,
P«
P«
xeton
HI
H2
H3
H4
H5
Bane

U f C )

154-155
162-163
140-141
187-188
124-125

15: Cdc pirazolin chiia hgp phdn hidroquinon (Pfn-s)

Rr
0.61
0,66
0.46
0,53
0.44
HiOusuJt
(%)
66
47
42
72
64
%N
linti
11.38
10.97
9.44
10.97
9.15
Inn

11.50
11.20
9.29
10,78
9.00

Phd hdng ngoai
Vo„(an')
3425. 3383
3414.3372
3283
3314
3288.3230

Phd hJT ngoai:
A,«("m)(k|c)
225(3.93): 310(3.85); 340(3.95)
227(3.48); 316(3.45); 344(3,55)

-222(3.90); 294(3.37); 368(3.40)

-Bang 16: Cdc pirazolin chua hgp phdn axit dehidroaxetic (PouAi-n)

TT.

PewM

PfHU

PoHU

' M M

Pavw
Pom;

PuM

P O M
' DWMO

PflHAn

P n « B

Pomu
xeton
DHAl
DHA2
0HA3
DHA4
DHA5
DHA6
DHA7
DHA8
DHA9
DHA10
DHA11

0HA12
DHA13

W^)

221-223
205-207
283-284
224-225
115-117
80-81
127-128
170-171
65-66
ISO-181
240-241
179-180
220-221
R,
0,60
0,70
0,63
0.66
0.75
0,69
0.47
0.66
0.38
0.40
0,52
0.50
0.49

Hi&usuat
(%)
75
96
93
82
87
91
87
82
86
89
72
70
73
%N
Tinh
7,27
7.01
6,07
7,01
5.89

-12,80

-11,09

-lim
7.32
6,70
5,68
7.31
6.07

-12.50

-10.72

-Phd hdng ngoai
(cm')
Vc,,
3400
3381
3450
3450
3420
3433
3429

: M 6 5

3452
3427

3450
3348
3443
Vcoc
1240
1244
1246
1245
1255
1253
1241
1265
1257
1213
1275
1253
1212

Phd t u ngoai:
^ ( n m ) (lgc)

218(4.48); -; 283(4,20); 424(4.17)
225(4.41): -; 344(4,36); 434(2,45)

-: 295(4.17)-; 392(3,85)
220(4.53); 285(4.13); -; 392(3,99)

-; -; 287(4.02); 354(3,69)
-: 235: -; 394
202.234; 296; 359

203; -; 284; 383
203; -: 284; 381
207; -; 293. 308

203; 252; ;
-202; 248; -; 350

201; 251:-; 350 1

</div>
(24)<div class='page_container' data-page=24>

uuriK M.

/_. \.u%. yuu4,olin chita vdng quinolin

(PQI^) 
TT.
Pu.
Paz
Po,
Po*

xeton

Ql
02
03
04

U^)

210-211
200-201
111-112

i7&-ieo

Rr
0,58
0.64
0.76

0.61
Hieu suat

(%)

*

58
64
70
%N
rrtfi
i:t.9
13.4
11.7
11.3
Tim
13,6
13.2
11.4
11.2

Phd hong ngoai
(cm')
Va,
3422
3416
3387
3450

V N H

3277

3281
3057

-Pho tu ngoai
X_(nm)(lgr)

221(4.21) -; 340(4.32)
238(4.81): 303(3,92); 341(3,82)

236(4,43); 297(3.92);
--: --: 341(4.45)

Bang 18: Cdc pirazolin chUa hgp phdn cumarin (Pci.9)

TT. 
P*c.
Pc
Pa
P M
P«
Pes
Pa
Pes
P«

xeton

01
C2
C3

C4
05
06
07
08
09

U(^)

258-259
292-293
328-329
235-236
241-242
277-278
188-189
281-282
200-201
R,
0,66
0.68
0.83
0.78
0.73
0.82
0.79
0.71
0,66
Hr^sual

(%)

88
57

67
75
70
50
53
90
69

Phd hdng ngoai
(cm')
Vc.
3303
3277
3211
3411
3118
3510
3482
3273
3472
Vc01ac»on
1710
1710
1700
1721
1747
1726
1726
1722
1726

*: PhA l i l - N M K . cS/7>//;: 2.4()(CI1,); .>,7() va 4. U) (CII.); 5.SO (IIC); i 1,10 (HO);

12,10 (HN): 6,20 - 7,70 (cac H nhiin therm).

MS: 435 (M'')

</div>
(25)<div class='page_container' data-page=25>

IV. I HAU LUAN KEI QUA:

4.1. Axetyl hod cdc phenol vd chuyen vi Fries cua chung:

•J* Ddi vdri cac monophcnol day benzen va quinolm chiing lAi thuc hien phan ling axetyl

ho^ nhom hidroxi bing anhidrit axetic trong su co mat cua mgl ft axil axit pholphoric l^m

xiic uic. DA'i vdi c«ic phenol dihidric (hidrotiuinon \a rcs(>:\inol) hoac hidroxicumarin cluing

t6i thuc hien phan ling tuong lu nhinig thuiifng dung axit sunluric lam xiic tac.

(Zac este nh$n dugc co nhiet dA nong chay phu hgp voi du kicn trong tai lieu tham

khao. tren phd hong ngoai cua chiing deu khong con pic dac trung cho dao dAng hoa tri cua

nh6m OH phenol, trong khi do xua't hien pic dac trung cho dao dAng hoa tri cOa nhom

cacbonyl este 0 khoang 1650- 1720c/?/'.

• Cac ddn xuat axetyl cua phenol dugc chiing lAi dua vao phan ling chuyen vj Fries nhim

tao ra cac chft't d^u ihuAc loai 1- axetyl 2- hidroxiaron. Phan ung dugc thuc hien vdi lugng

AICI3 khan lam xiic tac theo ti le mol vdi este 2: I hay 3: 1 tuy theo monoeste hay dieste a

nhiet dA 160- 180"C trong dung mAi nitrobenzen hoac khAng co dung mAi.

San p h ^ ciia phan iimg chuyen vi Fries deu la chat rdn va co di^m chay ro rang, cung

nhu c6 gia tri R, tren s;1c ki ban mong khac vcri csle ban ddu. Tren pho hong ngoai ciia

chiing deu xua't hien tra lai pic dac trung cho dao dong hoa tri cua nhom hidroxi phenol

trong khoang 3200- 3400c7/7'' va pic dac lrung cho nhom CO axetyl, thudng vdi sd sdng

nho hon cua nhdm CO este. PhA cong hudng tir proton cua cac san pham chuyin vj Fries

deu xuat ihen cac tin liicu cua uhdiu C l i r C O , cua hidro trong nhdm OH va cac tut hieu

khac phu hgp vdi cau triic pham tir (hinh 1). Pho khAi lucmg cua chiing deu cho pic ion

phan lir phii hgp vdi phan lu khA'i (hinh 2) va cho su phan manh phii hgp vdi ca'u tao phan

lir. IIH^ du: DAi vdi sin phfim chuytin vj h'ries la H- axetyl- 7- hidroxicumarin cd su phan

manh nhu sau:

CM.

O ^ "^Ctb
190

</div>
(26)<div class='page_container' data-page=26>

I I CS)

l-l

r-1

n.

T I

0
.11

1 1

,•_,

ty

o

u <

.::i 0

• x: m 
L;

a j a< - . I
tN 0 If)

0 . X D

n c E

1 OJ l a

: ^ - H

' r^' (•')

' i! '-^

H - ••
< U . - i

Q a rH

--- ^

.-( -U

''^ ro

I'li lU .-)

X o ra

U > i O ^

Cu cn rn CO

X C 2: cr^

^ ' ' 0 Iil

•• - c : i-Ti

CJ i-i.

u l
C

u 'a di

o OJ e

i-i U 'J

tO - H U 
OJ J^ D -U

H a) cr cji 
H a u c

i . O < n
r-^ 
P

[-1

L ;
0)

B

^ 
S

0)
,—i

a 
E 
m

o

ro 
n: 
(.)

-U)

5

• - ^
(-H

0
r/J r-(

H
(11

0 .0

^ E 
a 'J

h^ •^

U r-f

CQ 111
• H - H

s >

1/1

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V

'11

o 
o 
o

- J ' o

c:^

O '

o 
o

• 3

0
0
0

i n

0
0
0
0
r ^

</div>
(27)<div class='page_container' data-page=27>

IV. I HAU LUAN KET QUA:

4A. Axetyl hod cdc phenol vd chuyen vi Fries cua chung:

• D6i vdi cac monophcnol day benzen va quinolin chiing tAi thuc hien phan umg axetyl

ho^ nhdm hidroxi bing anhidrit axetic trong su cd mat cua mAt ft axit axit pholphoric lim

xiic uic. DAi vdi cac phenol dihidric (hidrcKpiinon va resoxinol) hoac hidroxicumarin chiing

tAi thuc hien phiui ung tucnig tu nhimg Ihmmg diing axil sunluric lam xiic uic.

Cac este nhan dugc cd nhiet dA ndng chay phu hcfp vdi du kien Irong lai lieu tham

khao. tren pho hong ngoai cua chiing deu khong con pic dac trung cho dao dAng hod tri ciia

nhdm OH phenol, trong khi dd xuat hien pic dac trung cho dao dAng hoa tri ciia nhdm

cacbonyl este d khoang 1650- 1720C77/'.

•> Cac dan xuat axetyl cua phenol dugc chiing toi dua vao phan dng chuyen vj Fries nhlun

lao ra cac chai dau thuAc loai 1- axclyl 2- hidr<)\iarcn. Phan ihig dugc thuc hien vdi lugng

AlCl^ khan lam xiic lac theo ti le mol vdi este 2: 1 hay 3: 1 luy theo monoeste hay dieste d

nhiet dA 160- 180"C trong dung mAi nitrobenzen hoac khAng cd dung moi.

San p h ^ ciia phan img chuyen vi Fries deu la chat ran va cd di^m chay ro rang, cung

nhu cd gia tri R, tren sac kf ban mdng khac vdi csle ban dau. Tren pho hdng ngoai cua

chiing deu xuat hien trd lai pic dac Irung cho dao dong hoa tri ciia nhdm hidroxi phenol

trong khoang 3200- 34000??' va pic dac trung cho nhdm CO axetyl, thucmg vdi sd sdng

nhd hon ciia nhdm CO este. PhA cong hudng tir proton ciia cac san pham chuyen vi Fries

deu xuat iiien cue tin iiicu cua iihum ClI^-CO. cua hidro lrong nhdm OH va cac tut hieu

khac phil hgp vdi cau triic pham lu (hinh 1). Pho khAi lugng ciia chiing deu cho pic ion

phan lir phil hgp vdi phan tu khdi (iiinh 2) va cho su phan manh phii hgp vdi ca'u tao phan

lir, Ilii du: DA'i vdi san ph«am chuy(!n vj hrics la 8- axclyl- 7- hidroxicumarin cd su phan

manh nhu sau:

I W

</div>
(28)<div class='page_container' data-page=28>

01 n

v> f-,

I.}

iJ ft.

v

M • • 
la t 1

l l . 1

ll) ( 1

f... .

L / )

l i

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t J

m

>

<n

(J f l l l U) ^
C r i if) Cl
' 1

0 0 0 ' 0

3 n.' X (•;
U ^ I.l n,

5 n 5

=-I A : a : 11; • i.i
<ii H ra 11. >

6 to o -1 ^1 X

' ^ 2 o ; ^ l - J O ^ / ^ W J S

tr't-ta.a.i-t/tz.ciin

! i.

' ) 0 /
HO 2

'Jib

e i b
fv:6

"'J

9
9
'J

/ 
/.

5 1 -IJ

' \

f/^

• H

\

0

I . ,

I) I

: . ' n i • I

</div>
(29)<div class='page_container' data-page=29>

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4.2. Tdng hgp cdc xeton a, fi khong no:

Cac xeton a, P- khAng no dugc lAng hgp bang phan ung ngung lu Claison- Schmidt

giu'a cac metyl xeton vdi cac andehit di vdng theo ti lc mol 1:1. lrong trudng hgp ciia cac

metyl xeton binh thudng va cac indol- 3- andehit phan ung dugc thuc hien Irong dung mAi

clanol vdi dung djch kiem dac (NaOH 60'/r) Ifun xiic tac. Cdn trong Irudng hcrp cac metyl

xelon cua axit dehidroaxetic ho;]c cumarin hay vdi hgp phan andehit ciia day fufural thi

phan dng dugc thuc hien bang each dun soi trong clorofom vdi pipcriddin lam xiic lac.

Tren phd hdng ngoai ciia cac xclon a, (i- khAng no deu cd cac pic dac trung cho dao

dAng hoa tri cua nhdm CO lien hgp trong khoang 1600- {GHOctn' va dao dAng bien dang

khAng ddi xihig ciia nhdm frari.s- vinyl irong khoanu *?50- 1000(7// ^ Ngoai ra con cd cac

pic dac trung cho cac nhdm chuc khac trong phan tir.

Pho tir ngoai cua cac xeton a, f>- khong no ndi chung cd 3- 4 cue dai ha'p lhu nam

trong vung tir 205- 225, 240- 270, 290- 340 va 380- 420/?m dac lrung cho budc nhay

TI-^TI*

va n->7r* ciia timg doan mach lien hgp va ciia mach iicn hgp keo dai loan phan lir.

PhA cdng hudng lir proton da cho thay cac Im hieu ung vdi cac prolon lrong phan tir,

dac biet rd net la lin hieu ciia hai proton trong nhdm vinyl d dang 2 vach ddi cd hieu ung

mai nha va hang sd tuong tac spin- spin J= 15- 16Hz, ma dieu nay ndi ien nhdm vinyl cd

ca'u hinh trans- (hinh 3).

Vh6 khA'i hrgng ciia m(Vl sd xclon </. \)- khAng no cung cho pic ion phan lir triing vdi

phan tir khdi ciia chat (hinh 4J.

4.3. Tdng hop cdc hop chat tuang tu flavon cd chira nhdn di vdng:

Cac hgp chat tucmg tu Haven cd chua nhan di \ong indol hoac furan dugc long hgp

bang phan inig cAng hgp ddng vdng de hidro hoa bdi luu huynh. Phan ling dugc thuc hien

bang Cclch dun sAi \\6\ luu suA'l 5 K gid hAn hgp ihco ti lc mol I: 1 giua xclon a, P- khAng

no vdi luu huynh trong dung mdi xilen.

San pham la cac hgp chat ddang ket tinh thudng co man sSni, cd nhict do nc')ng chay rd

rang va cd gia tri R, ticn sac ki han mong khac \di R, ciia xclon (x. (J- khAng no khdi d^u.

Ph(5 hdng ngoai \l\ tir ngoai ciia cac hop chat luong tu flavon thudng khong khac nhieu

so vcri phA ciia cac xclon a, p- khong no tuo'ng ung. 7 iiy nhicn tren pho hAng ngoai cua cac

hgp cha'l imnig (u llavon da lh;Vy mat di pic dac lrung cho dao ddng hoa Iri ciia nhdm OH

phenol va dao ddng bie'n dang cua nhom trans- vinyl, lrong khi do lai xuat hien cac pic dac

</div>
(31)<div class='page_container' data-page=31>

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lrung cho dao dAng ciia nhdm ete vdng d khoang 1130- 1160 va 1240- 1280cm"^ Cac dCJ

kien nky phii hgp vdi dU kien ve ph6 ciia cac hgp chat tircmg tu cd trong tai lieu tham khao.

4.4. Tong hgp cdc hgp chai kieu pirazolin chua nhdn di vdng:

Chung ldi da tien hanh phan ii'ng ngung tu ddng vdng ciia xeton a, P- khdng no vdi

phenylhidrazin de nhan dugc cac hgp cha't pirazolin cd chira di vdng indol, furan, quinolin

vk cumarin. Phan dng dugc lie'n hanh bang each dun hdi luu hdn hgp cua xeton a, P- khAng

no vdi phenylhidrazin trong etanol vdi vai gigt axit axetic lam xiic tac.

Cdc san phim pirazolin ddu la cac chat ran d dang tinh the, cd nhiet dA ndng chay va

gia tri R, tren sdc kf ban mdng khac vdi R^ cua xeton a, P- khAng no khdi dSu.

Tren ph6 hdng ngoai cua chiing da thay mat di dao ddng hoa tri cua nhdm CO lien hgp,

nhung vSn cdn pic dac Irinig cho dao dAng ciia nhdm OH phenol va ciia cdc nhdm chi'rc

khac.

Phd lir ngoai cua cac pirazolin da khac hin ve sd lugng va vi tri cac cue dai ha'p thu,

cung nhu v6 dang phcl Sd di vay vi khi tao vdng pirazolin, mach liCn hgp toan phan lit da bj

dut gay.

Vh6 khdi lugng va ph6 cdng hucmg tir proton cua mAt sd pirazolin cung cho pic ion

phan tiJr phii hgp vdi phan lu khAi va tin hieu cdc hidro phii hgp vdi su chuyen dich hoa hgc

ciia cac proton lrong phan tir (hinh 5, 6).

Cdc dii" kien ve ph6 da xac dinh cau true cua cac pirazolin nhan dugc la diing.

4.5. Tinh todn hod lugng tu:

v a n dung phuofng phap linh gAn diing bang phan mem HyperChem- 4.5'^" chung tdi da

xic dinh mat dd dien lich, nang lucmg lien kel va nang lugng loan phan cua cac phan tir va

tiirdd xac dinh ca'u hinh uu tien ciia cac phan lir tdng hgp dugc.

Tren ca sd tfnh hoa lugng lir cho cac trang thai chuyen tie'p trong phan irng chuyen vi

Fries, san phim chuyen vj. xeton (x, P- khAng no, flavon va pirazolin da nit ra nhung k^t

luftn hgp ll, lam sang rd ihem chieu hudng va ca che pijan tmg. cdng nhu ciiu hinh Wn ciia

cac hgp chat i6ng hgp duac.

4.6. Thdm do hoat tinh sinh hoc:

Viec thir nghiem hoat tmh khang khuin va cho'ng na'm dugc thuc hien d phdng Hoa

sinh benh \'ien 19/8- Bg Cong an \'a Medilalec Co. l.mt. theo phuorng phap dugc ghi lrong

</div>
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(36)<div class='page_container' data-page=36>

dugc diln Viet nam (nhd chat thir nghiem d ndng do thich hgp tren thach da nuAi ca'y vi

khu^ r6i do dudng kinh vdng vA khuan). Ke'l (|ua dugc gidi ihieu a cac phiin dudi day:

4.6.1. Hoat tinh sinh hoc cua cac xeton a, p- khong no:

Qic thi nghiem cho thay cac xeton a, P- khong no chiJa hgp phdn hidroquinon va

resoxinol deu cd kha nang khang cac loai khu^n Citrobacter fr., E. coli, true khuan mil

xanh va na'm Candida allncal vdi muc dA khac nhau d ndng dA 5mglmi (bang 19).

Bane 19: Khd ndng khdng khuan vd chdng ndim cua cdc xeton a, fi khong no ddy

hidroquinon vd resoxinol (50/d)

Xeton

HI

H2

H5

Rl

R2

R3

R4

R5

DRl

DR2

DR3

DR4

DR5

Citrobacter fr.

17

14

15

25

20

19

17

15

14

20

15

18

10 Dirdng kinh vong vo khu^n (mm)

F.Coli

17

14

18

16

18

15

18

15

19

18 True kintan mu xanh

17

16

18

16

15

17

18

15

18

15

17 Ndm C. alhirtil

18

15

18

15

17

18

19

14

19

18

15

18

15

</div>
(37)<div class='page_container' data-page=37>

(Tic xeton a, p- khAng no day cumarin cung deu the hien kha nang khang cac loai true

khuin mu xanh (Pseudomonas aureus- gram am) va khang k h u ^ tu ciu vang (S.

epidermidis- gram duong), cung nhu chdng nam Candida albical vdi mirc do cao d ndng do

khac nhau. Thir nghiem dugc dung vdi 50/// (mAt so trudng hgp sir dung vdng 2, lire la vdi

100///) vdi ndng dA xeton a, p- khAng no khac nhau trong dimetylfomamit (bang 20).

Bdng 20. Khd ndng khdng khuan vd chdng nam cda cdc xeton oc, fi khdng no ddy

cumarin

Xeton

Cl

C2

C3

C4

C5

C6

C7

Nfing d6

2,50

1,25

0,50

1,25

2,50

1,25

C:8 2,50

Dudng kfnh vong vo khuan (mm)

S. epid('rmi<lis

14

20 24

20

20

22

20 13

P. tiiircii.K

15**

25*

18

14 25*

16

18 15**

Candida alhical

20 14

20

20 17

18

20 *: Thir vdng 2 (vdi 100///).

-s*. 'llur vdng I (vdi 50///), dudng kinh \ong \ 6 kh;:aii la \5rnm\

Thir vdng 2 (vdi 100///), dudng kmh vong vo kJiufin deu la 25mm;

4.6.2. Hoat tinh sinh hgc ciia cac hgp chat (uorng tu flavon:

Sir thir nghiem hoat ti'nh sinh hgc cac hgp chat luofng tu flavon cua day axit

dehidroaxetic cho thay ca 5 hgp chai ma d vj trf 2 chira vdng furan vdi nhdm the d vi trf 5

sau day: p- nilrophenyl

(F„HAO, p- hromphenyl (FUUAA P~

clophenyl

(FOHA?),

nitro

(F^HAO).

va brom (Ftj,,^?) deu cd hoat lmh khang nam Candida alhical vai muc dA cao. Nhung chi cd

3 hgp chat (F,,HA5'

FDHA^^

^a

FOHA?)

t:d kha nang khang khuan S. aureus va Subtilis a m\xc

Irung hinh kha.

</div>
(38)<div class='page_container' data-page=38>

Co 3 hgp ch^t ki^u flavon chda vdng quinolin va vdng indol d vj iri 2 (FQ,, FQ2 va FQ4)

cd kha nang khang khu^n Escherichia Coli, Pseudomonas aureus (true khudn mu xanh) va

Staphylococcus epidermidis a misc 66 cao vdi nhieu ndng do khac nhau.

Ngoai ra cd 1 hgp chat tuong tu flavon cita day resoxinol

(FR,),

tire la di tu phan gdc

2,5- di hidroxiaxetophenon vdi indol- 3- andehit cd hoat tinh khang k h u ^ mil xanh dang chu

y-4.6.3. Hoat tinh sinh hgc cua cdc hgp chdt kieu pirazolin:

Chung tAi chi tie'n hanh tham dd hoat tinh sinh hgc ciia mAt day pirazolin chd'a vdng

cumarin va th^y rang 6 hgp chat cd kha nang khang khuan S. epidermidis (tu ciu vang- gr.

duong) va Pseudomonas aureus (true khuan mil xanh- gr. am), cung nhu chA'ng na'm

Candida albical vox muc dA cao va a nhieu nong do khac nhau (bang 21).

Bdne 21: Khd ndng khdng khuan vd chong nam cua cdc pirazolin ddy cumarin

Pirazolin

Pc.

' C2

PC4

Pes

PC7

Pc8

NAng 66

mgl5()/d

2,50

0,63

0,50

2,50

Du6ng kinh vdng v6 khu^n (mm)

.V. epidermidis

14

16

20

14

16

P. aureus

16 14

19

19

15

14 Candida alhical

20 18

19

20

15 G^n day, trong mgl lai lieu tham khao'*^' mang lmh long quan da Ihdng ke mgl sd

xeton a, p- khAng no hoac cac hgp chat khac chua nhan di vdng kieu cumarin, quinolin va

quinolon- 2 cd hoai linh chdng uu^i. lhu va va cluVng HIV. Vi vay chiing lAi hi vgng rAng cdc

hgp chat ma cluing lAi tAng hgp duac cung cd the' cd hoat tmh chA'ng ung thu va chdnp HIV.

TSfl nhien neu cd dieu kicn chiing loi sc licp luc md rgng va phat trien hirdng nghien cun

nay.

</div>
(39)<div class='page_container' data-page=39>

V. KCT LUAN:

1. Da nghien ciiu phan ung chuyen vj Fries de tren ca sd dd tong hgp cac chat ddu cho

cac chuyen hoa tie'p theo.

2. Bang phan ung ngung lu Claisen- Schmidt da tdng hgp dugc hon 50 hgp chai xeton a,

P - khAng no cd chda cac nhan dj vdng indol hoac furan IhuAc cac day ogienol va

isoogienol, axil dehidroaxetic, ipiinolin, hidro(|uinol, resoxinol va cumarin. Tir dA da

chuye'n hoa cac xeton a, p - khong no thanh hon 40 hgp cha't luong tu flavon va gan

50 hgp chat kie'u pirazolin tuong litig.

3. Da cung ca'p cac hang sd vat li, cac du kien phA hdng ngoai, tir ngoai, phd cAiig

hudng tiir hat nhan va pho khdi lugng ciia cac hgp chat long hgp dugc. Tren co sd dd

da xac djnh dugc cau lao ciia chiing.

4. Da van dung cac phuong phap ti'nh tfnh gan diing de' tfnh loan hoa lugng tir cho cac

hgp chat leing hgp dugc. 1 u do da lam sang ro ihem dieu kien, chieu hudng va co che

niAl sd phiui ung, tUng nhu \AC dinh c(n\ hinh hen ciia tiic san pham.

5. Da Iham dd hoat Ifnh sinh hgc cua cac day chat long hgp duac va xac djnh dugc cd

35 hgp chat lhuoc cac day xelon (x, (i - khong no, flavon va pira/olin cd klui nHng

khiing khuan va chA'ng nam khac nhau, trong dd cd mgl sd cha'l ra'l dang chii f. Ke't

qua nay se la lien de cho su nghien ctru sau rgng hon ve hoat tfnh sinh hgc, dac biei

nghien cuu kha nang chdng ung thu va chdng HIV trong tuong lai ciia cac hgp chat

ma chiing tdi da ldng hgp dugc.

VI, KlfeN N ( ; H I

Vdi kinh phi va lluri gian cd han, cluing tdi da cd gdng hoan thanh mijc lieu, nAi

dung, nhiem vu cua de tai va da Ihti dugc ket qua lot. Rieng phdn hoat tfnh sinh hgc mdi

dirng lai d miirc tham do djnh linh klui nang khang klman va chdng naiii, Vi vay chiing tdi

mong mudn dc tai nay duac tiep tuc nghien cuu, v.v^ rong va phat tr'Cn. dugc chuyen ca'p cao

hon de' c6 the nghien cihi sau hon vc iiial hoai ii'iih sinh-hgc nh«im dtra den nlntng ung dung

thuc te'.

</div>
(40)<div class='page_container' data-page=40>

TAI LIEU THAM KHAO

1. Phan litig mang ten

2. O.A. Reutop, ^Theoretical principles of organic chemistry', MIR. Moscow- 1970, pp.

602- 604.

3. Dang Nhu Tai, Ngo Thi Thuan, 'Tong hgp Hod hpc Him ca (bdn dich) ", Tap 1, NXB.

KHKT., Ha ndi-^ 1982, trang 207- 210.

4. Hoang Van Hoan, Ludn dn phd tien si Hod hpcy DHSP. HNN 1991.

5. Nguyen Dinh Trieu, "CAC phuang phdp phdn tich Vdt ly vd Hod lf\ Tap 1, NXB.

KHKT, Ha nAi- 2001, Tr. 55.

6. Nguyen Hiru Dinh, Tr^n Tlij Da, *Ung dung mot sd phuang phdp phd nghiin cmi

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(BASF. A_G) Ges. Offen De. 3 402 732; C.A., Vol. 104, No. 4, 34065f (1986).

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11-13(ch): C.A., Vol. 109, No. 13, 110300z (1988)

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npoM3BOAHbie 6eH30 [ f ] xnHonnHa. CMHTea M cneKpanbHO__

/iH)MMHecueHTHbie xapaKTepMCTMKM" x . i . c , NO, 1 1 , c . 1 5 3 6 ( 1 9 8 5 )

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cneKpanbHbie xapaKTepucrnKM aueHa({)TeHOBbix 6eH3o [ f ]

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H i - l r i i i i i i i ; i ( h i ) t 1.1 l d i , 11 . i c . i i i r r u i i i . ' n , , n w.Ac\ h y M i i p j . i i i y \ ' o h . i n i i li y .

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(miiitiltu MXJMJ', [ililiii l u l o i iiO.p ( h r o c n : > i i i ) i i
f',. | | - M I O J I J ' . n o d u ( / ' ' «'lny',\'ii l l n ' m h t .it- h i f p i h.'il

iififiij'. I U ( ] ; i \ ' i i i i h ' j . M ' I -it ( h . l l I i ' ' ' i j Ml . i . ' i ll 111

lifi'nc, ifn|'.. (."Hti IiiH- i i i i i < .\. ;.,'m [>li:iiii .!.• •Ni.u 
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IM:I| II'MII I I c d i j ' I liM:in i l u .

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i | i n n i ' h n ,

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X - . ' l y n d n - . i ; , i m d l i . m : . h n i n : . l n m 11! -.(mic ( / , ( j - m n a i l n i ; i t i : t l h c n u u : . - . , 11 m l ; i i i i i n | :
i l i d o l i ' n i d ( j n i i H i I n u : i m y ; , .

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11;'.1.11 111,my. l i n h l l u / c i d i l l n m j ; c. i: p h : i n

/.Vi d i i I ' I ' -'/',,' '.l\ I I V . n l i t ) I 11,1 i ,• I M i n / 
l i n ; ' ;•. I I . L i t i h i.\\c.

I ' ' c - / , , ' i i - I- a / I ' l ' l i l i - - . : d III- I' i h - I ' l t .• i , i ( , i • a m i r . M i ; i d i , n i u - m ( i i I. N p i - i t i fvll'l 
h n . 1111' \ M i i t j n ' . I M l ' i l , i l v i n i . ' i i i l i i M i ' . .

•"\'"n r.'.'/ //iiii I'/iii, 'I'l.in 1\ ir.i I hi.i, I lo.'ini; I'ni.'i Tli.inr,, N''\iVi';i Win T..11,

.\'l

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HOA MO I SO \ i ; ION w.|i JvMON(; NO III ( A C 3 - ^ ( ) ^ n M N l ) ( ) l ,

VA i)Ai\ \ [ ! A i O ( ; I 1 ' ; N O L

(Synthesis and transfortnation of chalcoiiG analogs, containing indole

rings .IX. Synthesis and transformaiion of some f/,[l-unsaturated

ketones from 3-fortnylindoIes and derivative of eiigenole)

Xrjivfi Mmh rimii-. I'Juitn \ nn I'jumii.

A liiui //tin tioi - / I unnv H.u //... A hi>,i h,>, In nhu n - Dili liof (Jiun yjn l/n i\oi

l i v I . J i i r l r i r , , i l n i i i I ll . ' , u r l \ l> ii;-. M. J, . n l i I |i ,M ii >, 11 iii li ih '. di<- ' . r i h"'. t >( i / , ) ' . i m s n n i i . i l i d
l . c l i 111. •.. t . m l , u n t i i j ' i i H J . i h i i i i | " . I i . i v ' I M . 11 | ) n | i . i n . ! i - l m l i h , i \ i ' I t f . i i i (. I I M I I . i ; ' . i i . i l . i l
Iti ill.- t n i i f s p i i n i l m j ' . m . i l . . ] ' , 111 l l . i \ - i i i . m n ' , i < l i l \ n u i ". iili | > I I M I \ l l i \ ' I n i / i n . ' h • y n .•
iti<lt)l v l j i v i . i / n l i i u " .

r i u ' • a i i i r l i i u ' n l p i t u l m n, \^.^•. ,|, n i m u h d h v IU , ( ' V ' . p r i ( i n s r n p v , r l r i i n i i l . i l I I I I . I I V M ' ,

,\\\*\ d i m I . I M I r l N i i n i . u . i j ' n i | i l n .

1. IVI(') DAU

TiOiit; iiH>( s o con;.' I m d i li m i\ . l n \ | 1 -'^ |, c h i n i ; - li'u tin HID In \'o .sir I ("HIL: h o p c{\c 
x c l o n (/,(i kluMig n o va c l u n o n l u m rlniiii', llmiili imo h o p oh.al lifoiij: hr lliivon h o a c
Ciic h o p d i a l kioii i n d o l y l p i i a / n l i n

N h i M l i i l)i('d nhuMi il,an \ii.ii ' a m i m i o u d l hi m n j i o ' p oh;'!! ca') h o a ! li'nh s i n h h o c
(cho'ng; n a m k h a n y I J i i i a n i m \ I i. ii l l i n l i Midi i n n u i y . ihiiL" \'al .. ). M a i k h a o . oao
l l a v o n I h i o n n l i i o n (.•imy la i i l n i o : ' . Ii.a o o iniioii liidi vlial l i a n u ohii \', d a o hiol lion:-;
nhfrii[^ itaiii I'.an okay, itini \< ( m o ; ' . l a i n ; ' da iho h n a i IIDIII Iinli t hi'niy' \'! tail MIX'' | ^ 
-K|. C^hni? oaii M!'i i h o i n i.aio' iilio n nio.ahnl \',i lihirny hn'p o h a l k h a o o o ohir.a v o n ; :
i n d o l (la tlinto d u n n , l.aMi ihiio,. d i o o •ID,! ho:tl ( k i n " ni'in ho ih.an k i n h (iinii: ifo'iiy, lio;io
c h i r a h o n h l i n i niiic h

\ ' i v a \ ' IMMO', otHO' iiiiili i m \ ' hnii!' im l o d n o i i . a m MI v:;\ . h n i y o a o ph;in d'r
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h o p d i a l .

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ihir-hiiin a x c l y l lu)a (yijicnoj va lan d a n i i o n l i o n h.anh o h n y c n vi I'rics d o i vi'/t (fi^icny 
axelal do 'hanh / ' ' - a x t . d y l o y i o n o l i h o o p l i i i i i i i " h m h ph.in lin;^ san tk'iy:

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d:U" Irirni; ol.o d,ii ^ d t i n y Iit);i 11 i • im nh. noi ,i. lc m . i l i n i h u p I'i k h o ; i i y " I h2() 1 f)6.^ 
cm'', v a c h d .o (iniiy, o h o i d n n i i < d i phoni d "• '>ld() - H ' d ) o m ' va tlac hic I co \'ach

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- lOO.S c m '. N u o a i n i i r c n pho i i i m . ' ai \'aoh tiao d o n y ho;i l i i cic.\ nlu')m N i l - indol

l i o n g v n n i ; ^ 2 0 0 - i2.S() c m V

T i ' c n p h d li'r njA*'*.'" *-'i'i'i ^"'^^ x o i o n (/,(i kh()n)', no ( ^ l i i I r o n j ; d n n ) ' nu")i c l a n o l ) 
Ihrnmi^' I h a y 2-.^ circ tlai hap l l i n Ironv, vim.u 2.^K - 2'l(), 251 -26S va '2})^-^\.\ n m Wii

ht .so lal p h a n li'r k h a !(/n (I;', K \ f i ' ' - d,.S.\). d o Cu') dac l i u i i i : c h o hiroc nhay

e l e c t r o n 7 1 — > ? ! c n a l i r n u (loan m a c h lion l u i p hoac cna l o a n phan li'r.
K(}*l (-in;! dno'c i d n ('i h.-'my, I

T i r c;ic x c l o n (/,(5-khon,u no o h o n o h n n u l o i da llurc hiiT'ii sir ci}\)y^ h o p d o n ^ v()iu: 
t l c h i d r o hoa IxVi l;ic n h a n lirn h n y n h irony, d n n j ; m o i x i l c n (.lc n h a n diroc m()l d a y c;ic
l u / p d i a l l i i o n j i lir l l a v o n Inon;*, imp,.

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ni(')ng kli^K: V(^i cac dir k\ci) Iiuui!,!, nn_}', ci'ia \ c l o n han di'ui. T i c n p h o li(')nji n).io;ii cna 
c h n n g \\\\ \'an cni) v:\c\\ d a o d o n y hoa h i L I I a n l n n n ("() lien h o [ i a I 6 2 4 - I G'^H c m " ' , 
nlui'nt'. '\A m a i d i v.n h • l.n 11 n i i " < In < dm > . Ii >ii" ho.i 111 t I'la iiht nn < >! I p l u a n d . diSnr

i h o i x n a l Ihon cao \'aoh dao [ o i i i " oho d.ui d o n p hoa h i d t n x n r n : \'a hai d(>i \un_u cna
nh('>m clo v o n j ! hoiii.^ kho;'in:: I I '•>i^l \75 va 12 10 d 2 6 ( ) c m V O i c n niiy cluin,u l(') str 
cl()iig v o n i ; da d i f o v l l i n v h i c n I ion jtho \\f n p o a i oiia ciic ju/p d i ; i ( \ita\\j\ lir l l a v o n 
vAn c(') 2~ ^ one d a i hap l l u i i r o m ; VIMIL' 2 1 l - 2 i d , 2S,S - 264 va 2 ' M - .M2 n m \'iU hC .srt 
lat p h a n l u k h a l(')'n (l.ui: - 4 , 1 0 4,71 ). O i o n nay hoan (oiui phii h o p V('M c i c d\f ki(Jn

vc plu") In m.M »ai ona oao tn 'p ohal d a \ ' I kix'oii noi i lonp \ ;i r i a \ o n o i l inn o h n n n

K e l (pt;i d u o c I r i n h h;i\ (t h m i ; ' 2.

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vach iku) d('.>nj^ dac i i n n y oho n l n n n ('( ) lion h o p so \ari pho ona x c l o n han d;1n. 
nhirny, lai x n a l h i c n saioh |)ho dao don!- hoa i n oi'i.i I I I K M I I ( ) 1 I p h e n o l , n ^ h l a lii \'ach
ni"iy j o o n p sari pin") oiia \ i Ion n l i i i ; i y Idt.ao \ ( n pho nronu l i n u cn.a h o p d i a l lo.ii riavnii.
C o n p h o In iij^o;n l n \ ' oo 2 ^ i\\c tiai h.ap l h u iihnny. i h u i i : ph("> va \\ h i ' cac circ d;ii tlfi 
k l u i c nhic'Mi .so V('/i pho t. I'la x o i o n o .| i k l i o i i " no i n o n y irnu.

\ ' i ' i oac dir k i c n pho n i m v n \ ' vn kid (pi.i ph.in l i o h d i n h lironi', niio', clniny, \C)\ cn 
Ih(} t i n Hr('ynn mnp, oao ',.111 p h a i n nhan i l i i o o dww^.: nlur dtr kii"'!!.

I I I . K i i M A N

N l u r v a \ ' , hanj', sn ohii\a n \ i l a i c s o n i o n \ ' l ; i \ o i a l vol llurc h i c n n u u n ; ; In s;in 
p l n l i n n h a n d n o o v o i i .n •; h n n y h n d i d h o i i " m m l i i m n j ' , k i e m m a n h . eliiinj', h'li ilfi
U")!!!', ho'p d i i o c m o l ( k i \ oilo x c l o n i/,Ji k h o n y no o(') d u r a V(")n!' i n d o l vii phAn j[{)c 
(/jLiicnol l i o n y phan tn l i o p ihoo oao \ i ! o n (/,('. klion;^ no niiy dir(/c i-hiiyc'n linii
l h a n h oac h o p t h a i h i o i i v In M.aM-n hoac 0.10 h o p ohal k i e n i n d o l v l p i i - a / ( d i n liroim
i'rng.

Cac s;in ph.i'ni da dnoo dn d i c m o l i ; i \ , \ a e odnh y.\:\ l r i R, h o n sac ki' h;'in miMig, 
dirov d i n h I n o n g n i i o \'a \ a c d m h oan l.io iih(> pin") lu')ng n g o a i va i n n g o a i .

C('in^ t r i n h dirov h o a n ( h a n h xati a: hn h o ( na < I n i o n ^ l i i i i l i N g h i e n cifii Khoa hoc

I o h n i i l l o n ; ' h n h \ i n I v l n n i I n n I if l i l i i r i i .

I A I l . l l d • M,A,M K I I A O

N g i i y i a i M i n h d l i a o . I 0 I )IM1I d'niiiy, d'it\'on lap o.io hao cao khoa iioi.- lai i i d i nghi Khn;i *

hoo T m o n y i )l I K I TkN I '11(2' -I IN ''i^iM- I nam MdX. irang 10^. .j

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(53)<div class='page_container' data-page=53>

2. Nguyi>n M i n h ' l l l i i o . Np.nsaai d i m I nn, 1 nmn I n 1 lion. [ Ku]ii Nlur d'.n. I';ip (-"In I k^a hoc,

32. N92, d2, I W 4 .

3. Nguyi^n Minh 'lliao, N[:iiyt*n D m h Tliiinl;, Dan;: Nlur d a i . Dang Utan- d l i a n h . Nj^uyon

Vi(^t ' l l i a n ] ! . IIoi"ing T h i K i m \ ' . i n , Ngnymi d'lut Lan, I'lian Van ('ir. dap olii I !('>a hoc. .^5,

NQ33. 17. I W 7 .

4. Nguy(5n M i n h 'Hiiio. I'lian \ a i i ( n. Npnyiai I 1,'n Von. knp i hi I kia lio( . .V.. N9'\. 2. I')'JS

5. Nguyen M i n h d h i ' i o . Npiiyon d i m I ,iio l i.m;' O)ii<io d l i a n h . Ohaii \ ,in ( dr. Tap ^ ' i ' " " • '
h(H-, 37, N " l . V2. I')')'>

7. T . M Mo Koo, U.K. li.il OM l l , I I Ml ( '.Miin. l l . ol nl, I. Naliir,al I'lodnois. M). N " ' \ d ^ 1 .

1997.

K. Y- M . Din, I k Anderson, M d ' . I l . i v i n . o i ak, I. Naimal Omducls, 60. N^9. XS4. 0)97.
9. I I . T K i n o io 0 . Wam, ( "h ( ; Sinn I I , O.nl <av al, I Nnlnial Orodnols. 6 1 . N^ I , Ida.

I99S.

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^

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(54)<div class='page_container' data-page=54>

I d . Nynyr/i Xuiin I lu/ir. rh.n: in' , un. I'm .\n,i/! I/i.'/nli

i n v c . s l i e . u i o n o l Ihe a d s m p i n n i n l t i l i h o s o l h o n w m e i a l s on d i a l o m i l c
a n d using l o r c n v i r o n n i c n l a l h c a m i c n l

\S. Do ()n<ifi:^ Tnin.ii, Niiuycii Thi Inii, / V i g n v / / Xiiaii Dnnii. Cliti Xudn Anh

C o n c c n l i a l e d o f dVacc M e n m v (11) on . X i o h r c l i l c I 1 M 2 0 and
C h c l c x d O O l'.V;:,ms

16. Nguyen Win Nni. llu S\- r\rn. i •• \ in llnn:.;. N^imrn .\u,in Duni'.

Phoni Niinvi'-n ( 'hu'onv

D c c o n i j i o s i n g org.anic ( . l i l o i i n o i o n i p i i i n i d s in d r y t d e a n i m : waslcv.'aler
hy I ' c n l o n ' s icacdion

17. 'iiinh Xn(/fi .Sen, To Thi Ihiii}] 2: is/. Ny.uvcn Xmui Hoan

I r . l i i h i l i v o cITcLd o l i a ) i n p o n i i d ( '.\{\-\i),), k n iho anodic p o l a r i / . a l i o n ok 
s i e c l CAW in Ihe .solnlion a i k a l n u in llie j i i c s c n e c o l c h l o r i d c ions

IS. I*ha/n Van Nhicn

Sllicly and p r o d i K - l - o n ok e a l e i n m I nhiaoaliny * iroasos

0>. ( \)<> The lid. NyjiVi'n I >inli ILm. I o i im (, ^ n ' l / \uh:. 11 iid/i}: I'huiH IJII 
A d v a t i c c o x i d a l i o n piooossos .an .alloi n.aliv'o * l o r o x i d a l i o n o l

r e c a l c i l r a n l organi(-' c a i m p o n n d s

20. fj.hn Nyoe TInrni. I A- \ n Sn.n

C'Irbicc' ok Ihc hase, a p j i r o p i lalo m k h l i x o s and piop-aic Ihc Inkn loani i o i
t r a i n a x l e hcai inp,

2 1 . r/iani llouny, Nyoe, IAIDI N:-;[>e Tliir/u

I n v c s l i g a l i o n on ihe ( i a g , m o n l a i i o n i d / - loli a h i d n j p a l m a l iiic in die
w a s l c s ok " r o u g h l o l n n d i n " \)\' Mas-, ,Sp

22. Dony Nhu'Tai, T/ieu Tien II,). I un \ an /».'/

• T h i o c a r h a m o y l a l i o n a n u i i c (Dniaimm.', (ka ivali\'e,s. IX T h e
I r a i i s i b r m a l i o n s ok N a i y l i N \ k T d n d h v l l l n o t n o a ' ,

2 t. / M / n , ' Nhn:Tai. Tran Thac h \ iue Nynyen \'an /Vyoo

Synlhcsi.s a n d in\a'sl in al ion i d la n i O M O D m h i h i l n >n oap.ihthi N i d
N c l i i l l hascs l i a \ i n g h o n / o l l n . t / t do, h o i i / o i h i . i d i a / o l o and rndolo i \\] 
2d. Ngnvc/i Minh Tluio. I'liani 1 (/// I'Li'/i};.

Synlhcsi,s and l i a i i s l o i m a l m n (d oh.doono a o . i l o y s , o o i i l a i n i n i ' i n d o l e
r i n g s . I X . Synlhcsi.', and h a n s l o i m a l i o n o l some (/,,|l-nnsahii"a(cd
k e t o n e s IVom . i k o n n y l i n d o l o s and d o i i v a l i v o (d o n y i a i o l o

2.S. Nynycn Dinh Tlien. Than hinh I on;.'.. Dan Thi ihanh Win, I>oan

Manh Chill, Tran Thi ihwon): I Ihm

S y n l h e s i s , s l r i K d n r a l d c l c i i m n a l i o n and .csl o l h i o l o g i c a l a c l i \ ' i l i e s o l
some dct"i\';ilives o l ' 5-;iiyl-2-mLa.-ap!o- I, v d - o x . a d i a / o l e

26. Nyjiven Dinh irien, lh>an l>iiYiien. i'ran iliiihani: \'</n

IniVaivd spcdi-a ol" some k(>nim/ans o o n l a i i i m p p y n d i n c and cgiinoiin r i n g

Omie

sr,

9tS

101

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121

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(55)<div class='page_container' data-page=55>

2. Ngiiyc'in Minh 'Iliiio. N p i i y o n l i m I nn. 1 M.un I n l\ic[\. [ K\\\i: Nlur 'V.i[. k:ip ohi I l(\i hoo. 
32, N92, d2. 1994.

3. Nguyi^n Minh 'Iliao, N[:uyOn D m h T h i i n h , Dan;.- Nhu d a i . Dang OuOe d l i a n h . Nauven 
ViOl 'Miaiig. Hoang ' l i i i K i i n Van, Ngtiymi d h i i Lan, I'lian Van Cir. dap oiii I I('ta hoe. .^5. 
NO33, 17, 1997.

4. Nguy(^n M i n h ' I l i a o . I'li.an \ ' a n ( n, Npnyon I kn ^ o n . knp ohi I I(KI h.u . MK N^A. 2. I')'»S 
5. Nguyen M i n h dln'io. Npu\aai d Im 1 .no I )aii:' < jw^e d h a n l i . I'lian \'.u) (dr. d ap ohi' I loa

IKH:, 37. N " L V2. D ' ' ' '

7. T.C. Mo K(a-, I k l v . I'.id OM h, I ! ^dl ( tHiiiii h, ol .ll, I. Nalural l'n.dM( is, M». N'^"^. d M.

1997.

K. Y- M . L i n . I I . Anderson, M d'. I k i v m oi AI.^.I. Naitn.d Lmducls, 60, N'^9. XS4. 1997. 
9. Il..k K i n o lo K. W o o . ( I M ; .Shm, II I'.nl t i v .d, I Nnnnal LitMlnoK. 6 1 . N'^ L k l > .

I99K.

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(56)<div class='page_container' data-page=56>

iu

14
13.

16.

S.

0>.

20.

26.

Nyjiyen Xinin i ttOiy. I'h.ui I m , u'e I'm Xna/i I lianh

I n v c s l i g . i l i o n o l Ihe a d s o i p i n m a h i h l i c s o l hca\N mclaks on d i a l o m i l c
a m i using, l o r c n v i r o n n i c n l a l ire.aimenl

i)o (Jiuniy 'iruny, Nynyen ihi Ihir Nynycn \nan irnny. (Ini Xuan Anh

( ' o n c c i i l i a l c d o!' T r a c e M e n m v (11) o n A i o h r c l i l c 1 1 M 2 0 and
C h c l c x d O O Ke.sins

N.i^nyen Win Not. lla Sy l'\en. I e \ lei lluny. Nynyen Xuiin Dilny. 
ITiani Nyjiyen ( lufo'ny

D e c o m p o s i n g , oig.anic d i k n i n o i ( n i i j ) o n n d \ in d i y c l e a n i n g waslcv.'aler
hy I ' c n i o n ' s rcaLdion

'irinh Xuan Sen, ia Tin I lan:' .\,;a/, N}'.uyen Xuan Hoan

I r . l i i h i l i v o d l e c l o l ( a n n p o i i n d ( a(l J * ) . ) , Ioi (ho .anodic p o l a i i / a l i o n o l ' 
steel CT'4 in the s o l n l i o n a l k a l i i u in llie presence oT c h l o r i d e ions

ITiani \ 'im Nhieu

S l i i d y a n d p r o d i K l ' o n o k c a l e i n m I n h r i o a l i n v * Iroasos

(\lo'The Ha. Nyinu'/i I >inh H,in. I e < ha {>inh i ^any. inuhiy TImo'e iiU

A d v a n c e o x i d a l i o n prooesst s .ni alua nali\a- - (or oxid.ahon o l
r e c a l c i l r a n l o r g a n i c c o m p o n n d s

(Tun Nyoe ihiem. I.e \'n Sn.n

C l l b i c c ' o l Ihe haso, appiatpnalo n ( M i l i \ ' o s and p i o j . a i e llie I n l n i e a n l i o r
I r a j n a x l e hearinp,

Tham ilodny Nyne. Lain A'.','oo ihiem

I i i v e s l i g a l i o n n\\ ihc i V a g m o n l a h o n ol / - l o h a l n d i o p . d m a h n e in (he 
w a s l c s ok " r o u g h r o l n n d i n " h\' M a s ^ ,Sp

Diiny Nhu'iai. irien iien lla. I un \ an / M /

' I ' l l i o c a r h a m o y lal i o n a m i n e e o n l a i n i n g , (k i i v a l i \ ' e s . IX 'khe
I r a n s l b n u a l i o n s ol" N a r y l N , k r d i o i h y l i h i i u i i o a ' .

Dany Nhu'iai. Iran Thai h War Nyuven Win Nr.oe

S y n l h e s i s .and. i n \ o s l iy,.ilion o l t < n lo-m m m h i h i l nm i . i p . i h t h ^ i d
S c l i i i r hasc.s h a s i m : h e n / o l h i . i / t do. hon/t a h i a i l i a , a d o and u i d o l o i\\\

Nguyen Mmh Tluio. Tham \ an Tl.i my.

S y n l h e s i s and h a i i s r o i m a h o n o l o h . d t o i i o ao,i|ogs. (.ajnlainini', i n d o l e
r i n g s . I X , S y n l h e s i s and h a i i s l o n n a l i o n o l some (/..|)-nnsahira(c(i
k c l o n c s krom 4 l o n n y l i n d o l o s and ( k a i \ ' a l i \ a - (4 l a i g o n o l e

NyuyOn Di/ih Tneu. Than Path i^ny. Dan ihi ihanh Win. Dodn 
Manh Clu'/l. Dan 'ihi ThiOfny Duh'

.Synlhesis, s i r n c l i i r a l d c l e r m m a l i o n and lesl o f h i o l o g i c a l a c l i v i i i c s o f
sonu^ d e n v a l i v e s o l ' .S-aiyI-2-meoaplo-. 1, ^ d - o x a d i a / o l o

Nyuven Piiih Tneu. Doan Din' 1 wn. 'i)-an Du Thanh Win

InlV.ared spc' !ra ok.some k o i m a / a n s o o n l a i m n : ' p y r i d i n e and t|nin()lin ring

IOI

\i)^.

1 ! /

121

I.!k

ts

144

LSO

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(57)<div class='page_container' data-page=57>

• I

OAI HOC QUOC GIA HA NOI

i TRI/CINC OAI HOC KHOA HOC TLf NHIEN

TUYrN TAi^

CAC CONG TRINN KIIOA SSOC

KY NIEM 45 NAM NGAY THANH LAP

KHOA HO \ HOC

I •

TRUdNG DAI HOC TOiNU; HOP (DAI HOC KHTN) HA NOI

19S6~2()01

"Jlui eollt'elit)4i 0tf llw pfiUi'i'ilitt(j.\ {or V.7 ' <Attnunistivti ()<f

(T^Jiiintenl ftwttlitf

'J(}n»tO( </fnuuy,uii/ ! ^T)() 2i)() i

</div>
(58)<div class='page_container' data-page=58>

: TONG HOP VA CmiY/^N HOA CAC HOP CHAT TUONG TU'

'.. , ^.KHANCON CO CHtJ*A VONG I N D O L . XL TONG UO? vA

C n U Y H N HOA MOT SO XL/kON n J U R I I O N G NO T U D A N XDAT CUA

|, ISOOGH-NOL VA CAC INDOL-3-ANDEHIT.

(SyntJicsis and (ransforiiKUion ofclialconc analogs, eonlaining indole

rings. XL Synlhcsi.s and (ransronnaiion of sonic a,P-nnsalnra(c(l

ketones Ironi derivalives of isoeugenole and indolc-3-aldeliydcs.)

• Nguyen Minh Thdo", Trdn Vein Chien, Pham Vdn Phong

Khoa JJoii line- Trudng- Dai h.>r K/lTiV, DJ/Qd Ila m'li.

\ liy cofuirn.Milion of fi-n. c!v}\.s(H'iiy_rnolr wiih indole-i-aldclwclc.^ the snir.'. cf 
a,p-iiiis(iUiriJir(l kcfniws. roninintny. tiulnir nnr.s 'have hrrn prcpnrrd. winch have 
hern (Ichydi oycnntcil in ihc cni ic-pomliny. (irr/inys of flavour or rrndilv irinl with

lihr/iylhyt/nit/ir In };i\'r uidnly![iyni7ohnr.\ > 
1 hi' j>niiliicl.\ have han dclcinnncd hv IK-. lJ\e SpfrlKr^roiiv. rlrnn-nln/

nnaly\i.\ niid ihin Invn chi oniniiiyi njihy.

I • '

', Nhu dii bie't. nhieu dim xuAi cua (/gicnol va ksoagicnol co iioai ti'nh sinh hpc dang

I chu y, da <lir(pfc dung lam ihuiV (.liUii ht^nh Uo.\c rli.li kftdi ihlol) sinli IriMnn liitrc vfnl 1.2],

1 NIli(lu,li(7p clul'l chua vOjiig irulol cung dirac diing \hiu lJiui>c chua h6u\\ hni mach, ttiCn

; chinh hoat dung cun he lliAu kinh nung inm^^ lio.lc c6 liic dung ki'ch tln'ch sinh truong

thirc v5l nil gia ni. Vi ihe nt'u glic^p ii6i liai hgp pli.ln n.ay vao lrong cimg niol [iliAn tu ihi

c6 liie lao la cac Uap ch.'il di vdnp, iin'/i \'oi Imai linh sink hoc c() Ih^' da dang vh lliti \d

'• han.

; Trong mpt thong bao Iriroc dAyl^J cluing I6i (kl giai lliitu sir \6uj\ iiop d/ui xuA'l

• ci-axclykrgicnol roi ngtrng lu. no vol Ciic indol-.l-andchil dc' lao ra ni6l day cac

j xeton a,n-kil6ng no va chuy{'a) lioii t Ininp, ih.'uih ( .'n' lii/j> t li.'ll tU{Tnj;'(n flavon ohiia sa'ai):

indol hoflciciic (I.'iii xuA'l iiKlolylpir.r/oIin.

Trong (lure K-'cac xclon (i.fLklu^n!! no loai nay onng nlur cac 1K;P cli.'U ki(^u lla\'oii

ihocic d^n xuA't cua vong pira/.ohn co chi'ra di vonr, indol cung d6v c6 hoai ifnh sinli hoc

]\'6 nliidu niai- Vi vAy, dc- ii('''p UK hiroii)', nglii(^n ( IP; ii.V/. noni'. c6n|' trinh lii(Mi lai. chiiiif,

it6i trinh b.^y sir King lu/p cac xrioii (^(Lkln')ng no iir dan xiiA'i cMixciylksocrgicnol vi'fi nic

'indol-3-andchil va cliuytn hon chiing ih^uili car hop cliri'l lirong tu flavon lioAc cac dAn

jXuA't indolylpira/.ohn Ihco so do dui'ii d.ly;

(.m ' " ' ( ^ • ( H : • l , O H

1 cai^. d- ,,,. ' " ' ' \ : k . ,<iw,,u. " ' ^ \ k " Airi. ow-> J^Cix:t.,

XJ -\:;!^'^- i^^o.'..;- KJ E^^i^Xi

"1 ! , , ,, '

t n i / - - i r ' M , :M;CMCI

cn/.) ^ k (.c^':M, . |,„,,- 11

MU 0

( M/j J r.i.K.n-cM. I..-1 cn/:n»CM JI

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(59)<div class='page_container' data-page=59>

d d a y : Ind = 1) liidolyL3; 2) 2-inciyhndolyL3; 3) N-iiiclyliiuIo!yI-3;Tli - phcuyk

;i' Indol-3-andciiil va 2-inciylindul-3-andcliil nhAn duac bang sir foniyi hoa irvrc {\6\^

. indol ihay 2-mctyIindol llico Vjksnicyc[[41. NMnctyIindoL3-andchil nhan duoc bAng sir

metyl hoa Irifc tie'p indoI-3-aiitIchii bai dinictyl sunfat trong niPi truang kiCm[5].

' Isoogienol nliAn tlugc hang su cU'ing phAn lu>;i ogicnol lrong dung dich KOII .^0'S

d 180-185"C [6] vdi hien .suAi 'T]% (lhu j)liAn doan sui a 125-127"C/ Sinnd l;0. c('>

n'",,-1,5640 va cac pic nen plu') h{jng ngoai a 3512 va 3dd2 cm'(v,j,,). 1273 va 1033 c m ' {\\_

o r ) , cung nlur cac pi'c dac trung, cho v('jng tlumi \ J iiOt doi C - C 0 1500-1600 cin'^ .

Isoagicnyl axclal nhAn (Ur(/c h(Vi su axclyl hoa Isotrgjcnol bang anhidril axciic

trong St/CO mai cua xuc tac Cl I,(.'()()Ma(6| v<'/i lii("ai .-aiiVl H.V/'{.. .S;in phAin ca diC'ni ch.iy

78-79"C (Ihco lai lien 17|. l"^^, := KO"C); K, ~. 0,16 (h.'m nuMig .silicagcn. he dung nu:^

n-hexan : etyl axetat = 3:2). Vh6 h6ng ngoai (cm '): v^^^ - 1760; v^f,^. = I lyo va 1030. Plu'j

tti ngoai :X._/lgr. (nm): 213/3,dl va 2.'^V3.2/..

CluiyC'n v| Idics cna .ixmyhsm <j',nnoI dime ilinc hitdi (' ()()-0*i"( ' lidii;'. dnng int>i

inilrobciizcn va xuc lac AlCd, khan. Nhan duoc s.'ni [iliAm vi'a liiiHi

.SM.VI

3 I'/<'-. c(') dicm

i n 6 n g c h a y T 7 8 - l 8 0 " C . R, = 0.6L Plid h(-)ng ngoai(cin'): v,,„=: 3366. v,„ ^ 16LV llu-. lu

^ngoai: A^^.^gc (nm): 20d/3.43;258(vai) va 2H.V2/.d.

Cac xeton (X.fLkhong no duoc iraig hop bang phan ung uguiig In giua <>•

iaxctylisoagicnol v(>i Ciic indol-3-andclnl iiong moi iruong ki(iin inanh(NaOII 60%). San

ipha'm deu la cliAl ran, co nhici d<) lunig ch;iy va gi;i ni R, trong sac ki' ban iiKaig klnic \('ii

'chdt dflu. TrCn plu) In.'ing ngoai cua clinng cn cac piV d.'ic (lUng cho dao d(">nj'. luia ni cn.i

Inhdm O H phenol a 3367-337d cm '.cua nh^Jin CO licdi li(;[) a 1635-1633cin '. ciia nhom

'etc a 1242-1276 va I 150-1 160 cm ' . cua nhom NM,„,vi <^ 3169-3278cm ' vA dao don;?

•bie'n dang (iiia nhom nans-vmyl d 950-'260 cm '. Idu") lu ngoai cua cac xclon o.(Lkhong

Ino c6 2-3 cue dai, trong vimg 203-2 I 1, 234^260 va 289-292 nm voi h(i s(^' (Al pliAn tu kli:i

';ldn(lgE= 3,91-4,55) chung u') cluing c() iigiu^n y/K hudc ciuiy('in n-> ii\ Kel iiua dif(;(:

gidi thi(?u a bang L

Khi dun soi hdn h(;p di^ng phAn nV gam cua cac xeton o..(]-kIidng no d ucw 11,,^ \di

liru huynh trong dung mC)\ xiicn sudi 3<S-d2 gid da nhAn duc^c cac hop dial incrnj- in

flavon \.\m^g i'mg HI,.;- 0 dAy da xay la ph.in ung d('>ng vdng dchidro hoa dudi lac dnng

cua liru huynh. vSan phAm cung la chAt ian nhung co dic'in nong cluiy va gia In R, hoan

•toln kluic vdi tV, xclon khdi dAu. Tren plu) luVig ngoai da khdng con xuA't hicn pic dac

tnmg cho dao ddng hoa in cua \\\\(n\\ OH phenol nlur d xeton a.p-khdng no khdi dau.

K6't qua dupc ninh hay d l)an]', 2.

,' M6t hifdng chuy^in hoa kli.ac ma cluing lui ihnc hudi la cdng hup dchidial hoa

•d6ng vong gifra cac xeton u,(Lkhdng no H, , v('n [ihcnylhidra/an dd lao ra cac h./p dial

^•indolylpirazolin ( I V , , ) . .San ph.hn cnn!-, IA chAi ran nhung cd di(:'m chay vA gui In R,

'cung khac \'(n xeton khdi dAu. Ket (pM diri.e gnu ihicu .r bAng 3.

]\ NhUvAy. IAn dAn lien chung loi d.i ihue liudi su c hinx-n vi 1-ries d6\ \'n\ ivoogicnyl

''•axetat lhanlw'-axeiyhso(tg,icnok \\M\ so nj-ung lu cua san pliAm chuyt^'n vi nay vdi cac

'indol-3-andc'fnl da nhAn duoc mot dAy cic xrion r,„|Lkhdng no. ma lir dd di' dang

U u y C n lhanh cac lu^p diAl luong m Ike/mi r,, (Ink, v.mg mck>I IioAc cac hop rh;,i kicn

'Jndolylpira/.olin.

C\n \M) LU.i cac s.ni pliAiii <ka. x,u dmh [liio jlni h^nr, ni:o,ii. lu ngo.ii. cnni- ninr

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f l

T A I I I k d l 11 J A M K i l A M

't ''•'•-. ^ • •

f-^'l. Pham V a n i l o a n , Nguyen Van 'kdng. Hoang d l i i 'kuyci Lan. Nguy(:n I luu Dinh.

T- •' ^^ Tuyen tcip cdc cong trinh Uoi nyhi khoa hoc va cony iiyjic lloa I liru C(f. I lai ityiti

' 1 todn Oudc Idn ihu nhdt- Quy iihon 9/l*)99 l i . 1 I fk

f • r . • ' ; ' • ' • r ' I • . •

'[ 2. H& TJlii Diep. Doan Duy d'i("n. 'Www J\\\ \MA\, [A)\\\y(^\\ Oinh T r i e u , Tuyen la}) ede 
Cdn^ hinh I lai nyhi klion hoe vd cony nyiir Iind I liiu cif, I Ini nylii todn t/ude Idn

tint nha't-Quy nhan- 9/1999. ir. I.M.

! ' 3. N g u y e n M i n h Thao, l*ham Van I'lmng, Tuyrn u'ljj ede < any trinh khoa lun" Hot

'• ; . nghi khoa hoc Idn tln'r hai- nydnh Hod lue--1IHOOO. N X B D M Q G l l a inji. Ila not

' . . 2001.11- 138.

* • 4. G.F. S m i t h . . / . C//cm. 6'm-. . N ' l l . [i.3Hd2(lO.Vl).

: 5,. V . M . Rodionov, T . K . Vc.xclovskai.i, / / ; . Oh.s. Khan.. WZi). p. 22t)2(I9>Oi.

' 6. Paul Z. Bcndoukian, PciTunu'ry iind Hasaniiny synflu-ue.s. Fdscvicr [luhhshmu 
' company, 1967. [).361.

' 7. Hofulhook of Chenii.strv and Thy.sic.s. I'lihlislual hy ihc chemical tnhhct co. 
I • A u g u s t . . ( d ( c ; Dress klonda - 19()d. p.XO'g

</div>
(62)<div class='page_container' data-page=62>

I l l

M U C LUC

rt

I'nuh

, f^guyen fJi/ih lUon;, IIndny I hi HuOii}; llu'\ V('> Quyet ihdny 
'rdn[J h o p \'a, iigdncn i on |)lin( ian cn.i kniian \'('n valiii va L c u x i n .
Nguyen Dinh luin\:. I hu'iny'l hi llWOn}; lhu'-, ihuny lladiiy I .any

NghiCn crm'lA(di luai .sai \'a unmgaii lrong, i i i d l VA) ngudn lUftVc ng,Ani (V ha 
ll()i bAng Xi'ii.'i lac N'hi< ', nen Ihati hoai lidih.

irdn Kiin Den . ie Hnny,

N y l l i c n Ct'ui kha n a i l " l;ich hini < aiixi V'A magic la khdi mn(')j dung Iiong, 
cdnii n[jhc (hi'ai p h a n M i i - (du I'aiig. (pi.i i i m l i tua m u o i ,

f\lguycn>Xndii ll um;. Hut Xinm I li/nih. Iniii I),n I hanh

NglliCn Ci'tn ldi;i naiip, h.ap plm I huy iipan ( I I I . ( h i (!1) 11^11 ( hilo.'.nn.

Trdn Chn'rhh' Hnven. I .el hi I IUO/H' (iuinv. I'1 an ihi I loai Vdn

X i k d j n h hronp, \ c l :.clcn hang, phininy, ph.ip cue phd M\\\[\ vi phan sn d u n ; ; 
•stlng }\\\c liic.!

I.dm Nyne'l'h.e lid ,yin, Um

Njdlien ciin i > 1 clic ph.in nnn D M In I.I M U i l n i i n p l i n d a / i T C / o c M i i hanj' l i d ' ,
Iiong nidi InM'iig, l-,iciM (hnn Cn dinij', M K i.n laia M n ( I I ) .

Ni^nveti Qua Tudn. I u'u Du Hue. I'lian /V^iv'C / nan

PhAn ti'ch alkiidxin iKnig, lac. ii;ni v i ihuc an jna ,srK: hiUig, .sAc ky king hicn .siial
caodctctdoi" liUN'nh uuan)'..

Nguyen Ddt lim-. rihnn Nim ILum

Nghien Clin kh.i nang, h.Vp phu \'.i M K ; I.U phan huy mdi so lu/p d i a l cu clu c\\.\ 
I'liillipsilc In nhit n v u I nam.

ihanTdny, Xan. ie Inru Nhi. i'lian Maili (iuiny,, Nyny'-ii Vim Dau

Mj'JliOn CiVn hont t h.il 'anh Inn hi <ny hy llnnni {Sicyc.^hccfan m n-nUi/i.s \ ... 
A,';lcraec.ae) ( I M Vn-i I lam.

Moi Von 'iri. Tlnm iTny .Smi. I UiOny Anli I'luin. I.Uhfny Nym- 'I'u

I'llAll \^\-i 7 . 7 " . d d n u MicM'l.nin'iiiull.n .Ml, M-M hilKi\'un l i n d n . (n CA\ dh(">iig, 
^ (TaMts walhelmnni / . l u ( ) iiiu( u 1 .ww I Jung,, \dv;( N.ini.

Nyo'ihi'Thnan. Dmry. ihanh I n^m

I'lian i'rng phan ho kn luhu n l i e n >.cc Ln ' hici / c o l l i Idiij', hup In cnu lanh.

NyoThiDumn/iian l^'hii'Mn. Nynycn'iir." Dida

I'hAn U'ch .s/m pha'm p h n i mi-, d n - n In-.. I I'' • haii)' :.u- lu I In I,l;.n ph.. (( K '

MS).

Nynyen Minh 'ihao, iiduVan ( fnrn,ilnnn Van ilmny^

'IVi'nghup vachuyOn lu^; tac ln»p(hal luoni; l u Miaiicuii e6 d n k i vniii; i n d o l .

/.'

17

.?6

d/

n

•10

</div>
(63)<div class='page_container' data-page=63>

TRUNG TAM KHOA HOC T i i ; JHIEN VA CONG NGHE QUOC GiA

NATIONAL CENTRE FOR NATURAL SCIENCE AND TECHNOLOGY OF VIETNAM

40 NAM TAP CHI' HOA HOC

1962 - 2002

T. 40

1

2002

</div>
(64)<div class='page_container' data-page=64>

/ "

Tap chi lloa hoe, 7 . ^lO, .ui I. Tr. 9 - 14. 2002

XAC OjNH CAU HINH CUA OGIENYL AXETAT VA SAN PHAM

CHUYEN V! FRIES CUA NO BANG Pi

ILTONG

PHAP TINH HOA

LUONG TLT

nrn'l'nn .Minn 29^9-2000

N d l l Y h N M I M I I I H A O , j ' l l A M V A N I M I O N C ;

Khou Una h(H . 'ritioiiv DIIKIfiN. DIIQC, Ud Ndi

S l I M ^ ! , M • ' ^ '

Hv (/i/nnlinn mcduuiir:. rnh nhiln'ii (AM i nuthnd) luivc been dncitunal optimal 
COnfonihihnns i>fi>n>(hnl\ nnJ Iciuh in \ i'l I'lnw i cm.'nny.ciiiciil frofi ciiycny! nn'hnc into 
o-acctyh'uvciudc.

i

T i o n g coiij', n i n l i t i i n r day 1 1 | clnni)- loi da andchil nliAm (Aug \\a\) cac xelon (t,|i-kln^ng no 
c d n g bA'(jUii I r m l i a x c l y l hoa (()ncnol wx i liuycn v.';i chuyen li'ia clu'ing llianh c;ie liffp cliAl tifOng 
vj Fric.'i cua l u d d c lay si'ni pli.tm lam ( ha'i dan nr ria\'(,'n lioAc cac hop d i a l dAn xiiA't cua v d n g
Irong phan I'rn;', ninaij'. in xm <';n mdnl \ pii,'n'ulni.

a ^ l O - ( i i , f J

T

i i , ( i i r i i II .(11 c i p

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M g O . ^o t ( D C I g

< IPC 11-^'II,

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C J I / I U C I I ^

(1)

D ^ , d\i d o a n c h i d i dang c 
h u d n g va kha nang pli.'ui

umg cua t.tgicnyl a.sci.ii
CLlng n h u cAn n u c h i n l i
hoc, nAng h n n i g ya cau
h i n h hCn cua nu c n i i g ydi
san phfl'ni c h u y e n vi ki ic*..
l r o n g hai h;io na>', d n m g
tdi t r i n h l)ay kel (jua l i n l i
lOihi lu^a l i n i n g n'r W Wn nn 
li6a h i n h lu.'c hang plnani)-,
pliAp A M , i j i h a u m e m
Hyper 4.S) 121.

Dd'i V('ri (rj'Jenyi axelal
clu'ing l(''i nliAii (\ua^- hai

( I I )

liiitl) \e\ un k\ va 1,, dU'.ii dAy

i :

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dang pl)!\ng.

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b a y d b i n g 1,^ va 1,,.

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I r i ' m V vA I h e o d i u i u ( \ > ( d > d ; ,3^: ^ . j ^ . ^,J,^1J ^ . | „ ^ i , , ,„r^-.ng ph.'ni u n g c h u ) l

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ogienyl axetat vdi n h d m 
clorua. K^l (gia eung clio 
thSfy c6 hai danj.^ cAii iiMili 
ifulifin 11^'va II,,:

NhCrng thdng sd ve rriAt
dd dien Ii'cli, do dh\ \\(-u 
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va IIH khong ( un (k>nr, |iha(i:c 1 n-n d a ' V O ; nguv-ai cr uxi d i a nldnn C M , 0 - V('M vc^ng 
lech khdi mai phang, vung in n / m pan / . ym: hen/en hi giam han. Mat khiic, liCn kOd O r C , 
„iii (ij(-.,, ,.,,,;, (( Y,( ).d„, va \'>n;' iun/.-ii l.hu.ni,!' van n.nii W^^ivy mai i)liang vdng, ddng llidi do

</div>
(67)<div class='page_container' data-page=67>

dCt Am diCn IhA'p cua n g u y e n n'l n h o m nen niai

d d (liO-n l i c h irCn j i g u y c n nV ( ) , \.u\y len danj- kc 
( l i f (i,22 len -O.dVg Ixn ihc n m mat do dien
ti'ch Am d C ^ ( v i Ui ortlu;) len ldi - - { ) d 6 2 , nghia 
la Wm giin gAp 2 kin so v(''i m a i do t l i d i tfch Am 
d ( \ ( - 0 . 0 K 9 j va C.\(-0,OS;-^). Njnr vAy.'vc niAl ly
I l i n y i d CO die ,\;ir d n i h :.\i l.ni i um- i ii,i 
c i e c i i o p h i n cua C l g C ' t ) nu.i\y p!i,in imp, 
c h u y e n vi l-'ries) l.il nhien x.'iy la u \ i m oiilio 
( l u i ' la vao vi in' C,). i ^ K n ua\ hoan man jihii
h((j) V()i ket c|ua thuc n j d i a u : a \\ u i oillin- { d d i 
v('(i nlu'ini - ( J I I p h e n o l ) , n l i u n i ( ' d ((a'la nhom

/ I

" • - • • ( J I

I I

/. ^'J \

\

I I I I A 1

a \ c i ) l ) vua C(> su liOn Ua\) vdi nliAii heii/cin 
lao liCn k(:d h i d r d n(ii phAn l u vdi nlu'ini -{

\\('t\ vach liAp lhu dac h u n g cho no d plh>|i(

ngoai c d c u d n g dd g i i i m vA sd' sdng IliA'pIi 
h i n h Ihirdng (v,v,, = l d 0 3 c m " ' ) . Ngoai i.i.l
(jua tfnh loan nay, vci niAl l y lhiiy(:'[, CMiig g
phan klianj', d j n h v.ii Ii(d xi'ie l;ic c\\:\ nlii' 
c l o i n a khan I i o n g pinui ihig ehityeii \'i I tics.

.Sir ti'nii loan liep liie Ihco phuong phiip ;\!
('( l i c n d o i vi'ti s;in pIiAiii c h u y e n vi laics cii
xae d i n h duoc hai dang can h h i h ldi uu I l h 
l l l n d i r t ' n dAy:

( I I I U )

Nhuii)', lliunr, so M- in.ii d. - .!i>;n !u li. d.i d,n
hen kcl, p.oc hen k e l , nanp lihMii' dn<M i i i n l i li.i\ 
('/ hang d / \ va d l .

N h u vay, kei (|u;i i i n h Inunr, n'r doi \('n •.,'ni
[)ham c h u y i ' i i vj l a i c s {\\A <')'.ir[iyl .ixclal i h o 
Ihay:

- d'hi'r nhat: o a x c l y k / p i c n u l t (') i o n lai lien
kel h i d r o ii()i ph.iii t u gjir.i ngiiM-n n'r I n d i o ci'i.i
n h o m h i d r o x i \'oi n g n y c n in u \ i i na n ho m
a x c l y l . (') d a y . khoanp, cai h 11 .,() -- g o ' / : .-..
gdc (•.)dIO.. ~~ \y~': I I , ( ) , , d , . ' d ^ d . Ovd-'Ug 
plwing vA t;io lhanh luc y\Ac. l l i e u UKU ST) !;ic

ytA iniiM njni.'ii | d (hi lien kel lndn> nOt pli.lnl

clu Awvy Innh (hanh llini)n loi khi khoAnp. ^.\i 
( ) . , . l l nhd i i o n 2,(> A; goc O I K ) Idn hon 120 
do d d dlcu k i d i hoan loan duoc tluia man ili

\'di c;ie (l;ui)' l d i uu 111^, III,,. j

- d l i u hat: do anh htriVng cua IIIK'HM COm
mat do d i d i tich Am l i e n nguyOn n'r C Iron
I I I K M I I C I I , cna nhom a x c l y l c u n g lani; Icii I
n..'(>.M vi\ i\c d.nig. chnye'n lhanh c a d i a i i i o i i 0 
d i u h lam iliiian hd dn» ph.in ung iij',uiij; t
d k u s c n - S n i i t l i nep ihco.

- dlii'r ha: i f r c a c h a i i i ; s(") nhiel douyn

NhiCt l a o tliAnh

(Air's)

(i p i e m d axclal (I .^, I,,)
(CAC)

- 7 . i , ^d cV/()3 k c a l / n u d

S.ui pliAni I r u n g gian
( l l A d t n ) ( S n - ( i )

d5.'^..^21146S
k c a l / m o l

San[)hAin cliuyCn vi

(III,,. in,.)(SPCV)'

- 8 2 , 6 8 7 0 6 2 1 5
k c a l / m o l
I a m m . l u a plnin i\\\y Ik.nili '.' gi.n du.ni.

d .ID p h a * r l i i i N ' O i i \ I i-rliW'

\'Mc . ^ . d l M d ^ •SI'CV

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(68)<div class='page_container' data-page=68>

.Suy ra giai doan Uu; plnrc ..•. (gia Irinh t(')a
nhict.

D i d i nay phii hap vdi k d (|n;i iliuc nghiem: 
khi llK'm A l d l , khan vao cstc, n h i d do h6n luJp
phan I'nig lAng (hr nlii(d do pl.dng d d i 45

--f (liai tloan ehuyiai \'| nilhn- cn: All,,"

----82.(.87{)d2l.S-{-i.s.k.'kd I dr.;;); 7(),;vd(t.sdoi

(kcal/mol)

NghTa la gjai doan ( h u y e n /i niihn \;\ (pi.i 
I n h i h lhu nhitl't.

! C) dAy I All," I > I AM,," | iicn \'6 m.al ly 
lliuyci n h i d ddng j)han I'rnp ( hu>en \'i kries ci'ia
(igienyl axeiat co the lu x.i)' la. I'hirc te chi'ing 
Ioi da lidi hanh phan irng d nltu't do M) - 0l)"(' 
Ironp, vdng d gi(d va crinj', lhu diroc s/m nham
(dinyeii vj. d'liy nhien, dr mi ngan Midi gian
phiin lirng va lang hien sn.n Iiinh lhanh s d i
pham Ihi s;ui klu cho lud xTu l;ic , \ l ( ' l , \'.'io hon
h(rj) j)Iian irng can nang nhiel do jiliau unp, kai

1 10" 120"(^ va duy na tronj-, I )dd.

; ' Nlur vAy k d (|iia nnh loiin krong n'r IrOn d.^i
[ g(')p phAn giai ihu h vi sau i n m n ihn thrue s;in 
phani chnye'n sa u////u liunr i Inu'vai vi Iin-.-. lln 
' pli.ii lien hanh ph.in imp, u nhu'i d'* cat) (i.d)
' 180"(') Idk

K f d I.l iAN

;' Hang cAch tinh lo;in mai du dicn lich lien

cac nguyCn tu, dC) dai va gdc liOn kC'l gii/aci 
nguyen li'r, nan;.', luong t(Sn)', nanp. lu{riig lifiiL!
Cling nhu nhict tao thanh llico phuong phi
A M , , chung U)\ da xac dinh dune cac cA'ii lri 
hinh hoc un tien va cac dang can hinh b6n virc 
ciia (dial di\[\, s;ni phAm va chidi lurdnj: ci 
phan irng cliuye'n vj h n e s (f ogienyl axetat iliii
r'-.i\clyl((gienok

("d/i,i; Irinh ndy dirac hodn thdnh vdi .sif}i'ii 
ihi Hull phi t lid i'hiiony ninh nyliicii cdu U\( 
hoc CO' hdn Irony li'nh vi/c Khoa hoc tif nhicn.

d'AI I d l ) l J l l I A M KIIAO

1. N g u y d i Minh d h a o . I'ham Van Plion,
d'liyr'n l;i|.' t Ai n;i(» e/m khoa licK ci
d'rir(diig dai hoc Klioa hoc d u nhicn, 1)1 IQ
Ila Noi. lli,ing I 1 nam 2 0 0 0 d r r . 12d.
2. LAm Ngoc I h i d n . d'uycn lAp c;ie h'M) d

kho;i IKK' ciia d'liri/ng d.g lioc Kho;i linc'l
nhien. DI Kjd lla Ndi. Ihang 4 nAm 199

IY. Cd.

e r. M. (Ik'nnon, ,nul el at. .1. Ceinp ( liui

\'o!. IS. )*. lom - lodo (r)94).

d. l-)aiig Nhu d'ai, Npo d'hi dlniAn. dong he
lu'ia hoc huu ca (han chch), Nha xii.Vl hi 
Khoa hi.ic va Ky ihiifil lla Ndi, l(lp I, 1
2 O 7 - 2 I 0 ( l ' > ' K 2 ) .

</div>
(69)<div class='page_container' data-page=69>

T R U N G T A W K H O A ! i ( ; C T l f h h i i E N V A COixiG ^IGWf^ Q U O C G I A

WATiONAl. Cf'NTKl-: TOR NA 1 URAL SCILINCE AMD TECHNOLOGY Of VIETNAM

40 NAM TAP CiU HOA HOC

1952 - 2002

M'V' -'-J

U

£f%

</div>
(70)<div class='page_container' data-page=70>

Tap chi Hda hoc, T. -10, .so'2, Tr. I - 10, 2002

CAC DjNH CAU HINH CUA XETON a,n-KH6NG NO (TLT

o-AXETYLOGIENOL VA 3-FOMYLINDOL) VA MOT VAI SAN PHAM

CHUYEN HOA CUA NO BANG PHL/ONG PHAP TINH TOAN HOA

LUONG TLT

Dc'n'lda.sonn 29-9-2()n(} 
[ N ( d J Y H N M I N N l l l A d . P H A M V A N P I I d N d

! Khoa I Ida hcc. I'ludnv I )l IKI IIN. nilfKi lid Noi

S U M M A R Y

By (/uanlnni ihcnucnl cnlciihilioii (AM, niclhmi) have hccii dclrnninnl opliinnl 
conformation of a./l uii.\nluoiic<l kcionc {h<'i>i n iiicixlcuycmdc) and .sonic pnuhicls of Us 
IrnnsfornuiUon.

' Trong mdt .sd cong trinh IIu(>c (kiv I i M, '•"'"•ii kai luo n.ay, chdng ud tiinh hay

!., ,• ,^ ., , I • , , 1 , n l i u t ' n r nh.in hnh to;in hda lUi^ni'. lU (phuonp.
rhuilg tOi da tItOng h.n. ve .su (onp. hup \ . i i -• I i i , v - i . r i > d ^ \\\\ \i v d

° ph.ip 'NMi phan m e m 1 n r r . K d.S I l j ) nc xai. 
thliy^l iK^a mOl .so s r t o n u . j i kl.oni-, ^n^ d i in ^^^^^^^ ^^^^ ^^^^.^^^ ^^^^ ^^^^^^ ^,^^ ^j^^.^^ ^^^.j^ ^^^^^ ^.^^^. 
iJn xnAl cn;i (;gienul v.i c.i( . M u m y h n d o l ,|,,i,y,.,, i,r, ^i^ dai hen k e l , gt'K liCn k d . nang 
[fliig nhir ket tjuA n g l m a i ( i r u s u phan ho m a i p m n g \'.i * a.n h i n h lui uu t i i a x c i o n i t . [ l - k l i 6 i i g
idtlifin ti'ch, nAng h r i g i g \ic\) k d , can h m h l u i j , , , (,,;,„ pi,;[,,i np.uii): lu ciia rj-axely!oj',ieiiol V('(i 
ini ciia o g i e n y l a x e t a l va san pha'm c l i u y d i vi I d o m y t i n d o j ) va m o l sa s d i phAm ehuyCn hd.a 
Fries ciia n d cDnp, n h u m o i so x e i u n a,\\ eiia nd (iK-p Iheo c o n g l i i n h [ 2 ] ) ih'-o stf (\()

khdng no khac. [tluiu ung dU('A day:

d l !

^ âộ...^.^:::^^ ,.o)('iL

C l i o { ' I L O -

. ( • o n i - ^ c i !

// \

11 .Cl I " Cl 1.

Cl H

C I I : - - C I I C I l d

( I I )

( „

\-r'

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(71)<div class='page_container' data-page=71>

\ (Aiiip l i m h iip.hieii (am i ii;t c l i i i i i ; ' na nn,'/. n u i i lni.i hroiij', tir \\\ ldi uu In'ia hinh hoc xi'toii

day k d da clu ra ian;- . a n danp, hen , n,i car (/.,g-khong no (I) ciing eho hai dang s a i u i A y (I,, 
x c l o n (/.|i kh-aip no la linns .sci.'. ( ) (Liy Inili va I,,):

10

\\.^< f^

\

()

I •..,

\

;( A

' a 7

I 1

1 *

II

d ' d l Nan;> Inonj', Uaig: O^lOj W.,Sd I 88^ ki al/mol
^ n j < - / I N.tng luong hen Kel: -d8/.S.()2.r/dO.S k c a l / m o l

\ i N h i c l lao IhAnh: -d.7IS7d()S k c a l / m o l

'" 7/

, 17 1;,/

( I A )

( I

W^C

./ I

( I i )

II ' \

ll

\ I ' 'n
I I • "• ' "

II

I N,mp Inunp, UMig n.|0 11 ).o/o / />(, k r . d / n i o l
1 ,\,iiip. Inuiii: hen k c i : - d N / I . d d O C V O k r a l / n u d
I Nliua i.io [h.inh: d.LkS.L^7(. kcal/nud

II

' ( l i d

K('.| ,1)1,1 m d i Man \ t in.i; do d n n ii. ! i . d . ' d n ' a ' iliror l i i n l i h.iv n h.nii' 1 / \ [uwy. \\<'\ dani

dai li^-n k ' l . '.•••^ l i r a k e i . p.'. l e d i c u r nhi l A ' . . i I H o n i p v o u k n i g

kd-/„/,(/,' i A: ! u l (in.I l m h hrun:: lir r h u d.nig 1,,

M a i dt

c,

~w

'(\

c.

c,',

c:.

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o.i.d.i

o,.VM'

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11.1 ^r,
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1 \.---\."

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1 1 l,(>l
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I.d 1.77
1 I 2 . . i 0
L'd.h'J

( li 1^ I n !i (nlii d u a : , '*

( ) , ( ' , ( d )

( •,,,' 1 ( d

11,d,(',(',,

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(72)<div class='page_container' data-page=72>

Mat dA (liiMi ii'tli

ce.

c.

^ - U ' ,,

Cn
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,

c,,

C|., ,

c..,

Q. '

O.LSX
-0,222
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0,3 id
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0.012
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Q H
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-0.1d9
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d p d ,

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^

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( d - c . i i

. d , c d , ,
• <d' t d .

c , . (•,,,
('rr(\. 
d.ii-N
N-C,,
N-II 
(t,')72
l,d7.S
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l . d r ^ x

l..v|0
l.d ^(1
i.doi
i,d;d.
1.331
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I,d2 i
I,d(l()
I.'l.-t..'.

I,dd7
l.3')(.
l,,t.S7
I,ddo
I. ^No
LdIM
LdOO
L3S.S
0.')S.S

(iuc Ikai ket
l l d , ( d

< d d l
IlC.dl

^ V d d

d d • , , < ; •

( ) d d ( d'
C-nd,,(.d
f l / ' i / ' n
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(d^d^d

<'.n<dd,s
<d<V,(',>i,
d,,C,nN
C,,N(d,

N ( d * d
t ' . i 3 d C u ,
( ',.( • , . c , ,
( ' u / ' u f

^'nW.W.

C,„C,ndd

121.32
122.id
I Id,9d
1 21 .d I
I U..77
I I<),d3
120.71
122,00
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I Id,71
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10r,,of,
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10S.I7
IOS.9d
I Kk.v'S
I IS.NO
I I ' k l S
121,d7
12I.d2
117.65
I2S,84

/)dd,i,' //)': Kel i|u.i linh Inung ii'rchod.ini^ I,

MAl do dien lich
C|

c,

. ^''
Cs
; Q

'c,

St..

c,

C'„.

0,1 16
-0,206
-0,085
-0.085
-0.159
0,0.kS
-0,093
-0,154 
-0,228
-(),08()

0 6 dai lit
( d d ,
( > C \
d . - d i

(d<K

c\ C,,

(>„-c,

(.>(),

"""(), I k

(d C|,

•11 kei, A
LKK)
l , d I 2
1,385
I d Id
L3N3
l.kk''
I..i62
0 , 9 / 1
I d / 8
1. d a

(ioc he
ll,(),C,
()|C,C„
d d d \
t.d>id,„

d,,C;C;
d . C d 2 ,
l l d . C ,
( d d 1

l i c , d l

1 k e l , "
I 10.84
1 13,52
125,()d
1 15,84
1:4,03
1 18,()d
117,84
1 I'k'M
132,85
1 Id,98

C'dc lech (nhi d i d O , "

o,..-',c.c,

C , ( \ C M ( ) ,

(•,C,,C,;(
O.OS
.UlOf)
C,:CdC,,,C,
^'nC,,C,,(. 
^\^\C,i \

c.,WC,(\,

169.9()
18,61
99
f'7.58
klO.73

Cidc lecli (nhi dien), "

,0,C,Q

( k C C . C

( • ( ' / • , o ,

-5.44

.5(.

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(73)<div class='page_container' data-page=73>

M;)l cl(

C,

c,,

c„

C,,

^ I K

C|.^
C,o

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{k32()
-0,261
0,013
4),I51
-0.050
-0,087
0,1 d8
-0,114
•{),I38
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(\rW.-(:,,-(-:,.

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fd II

ai ke'l, A
l.d 69
1.348
1.429

1.4')!
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1,396
1.388
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( ' | ( ' / - ' n

C..d„C,;

O.Ci.C,,
_ / d f ; , : d , ^ _

I k C i d d
C,,Cdd,.i

f d ' ' u l l >

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d,s(d,<'u
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d , 3 d d , , ^

t •,.'* ' v f ' l .

120,96
119,99
119,43
120.71
120.68
1 14,71
126.74
122,11
106,57
106.28
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108,45
1 10,46
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119,37
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I 2 i , 2 8
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0 , C | C , C \

c,.,c>,c,.c.

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180
180
6.83

' l u k(:\ tpi;i n'nli lu.ui (hu>vn (hdudeclioii iiunp, c.i(du/p dial Iifrii cir

r d 'Tl

irtn thay lang:

, - d'hir nhai. cd idn Uu
lien kel hidi6 noi pliAn (iV
giua nhom hidiOxi \A
nhdai caclumyl vol kho.ing 
each' II....O ^ 2,0 A: goc
0,1 h'O, ^ 127". D i d i nay 
hoan toAn phd hop \'di kel
qua nghien ci'ru pho houj',
ngoai eua lu'i (\',,, " 163d
cni"'. ihAp hon a nhi'an ( () 
binh ilur(dnpd.

' - d'lnr !i,ii, mai da dien 
Ii'cli Id'n cac nhdm CC;

Cl'l~( I I eao nen kha nang i[,, ^ d
phan ung ( u a c \a to u.i> se ,, - ^ ';
Idn, ddng Ihdi k d (jUii uay / /
phil hop v(a ly i l u o c i II II

- dln'r h.a, cAu dang IHMI virng CI'M xelon (/,|)
khong no la Iruii.s-.

Nhung ke'l cpia nay kha phii luJ[i vdi cac
" ' ' " "7"^ ,^ "~tirr kien m^ig cac lai lid' diam khao | 3, dj.

/ Hang each ndih lo.in liunig tu, da .\iic dinh
diUK hai dang can hinh ldi uu (Ik, vA 11,0 ciia iu.tp dial lirong lu 
ri,i\on (Il)-san p h d u chiiydi hi")a cua xelon (x.p-khong iio(l) Hen.

dC

n'^^ft

()

J^isJ

()

N-!d?i/

( l k \

\ Naiig luong tOng:

-94265,2988043

" " " kcal/mol
a N;ing luong li<:ii ket:

-d752,27d6683
kcal/mol
-I Nhiet lao iJK'nili:

</div>
(74)<div class='page_container' data-page=74>

MOI (l() (liOii (I'l-li

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(die lech (nhi dien),

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1 15,80
125.20
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1 12,16
123.69
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122,15
I Id,59
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1 19.37
I Id,18
123.11
122d6
123.09
I 16.88
i:6.d2
i : 8 . u .
107,09
106,03
108.22
108.56
1:5.37
1 10.(10
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121,50

C(')C lech (nhi diiiai),"

C,„(),C„C\

('.('TT.

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d , ( d ' i i < k

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136.42
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(75)<div class='page_container' data-page=75>

MAt dd dien licit Oo dai hen kcl, A
N-II,

^ N d d ,
C . - C , ,

0.985
1,386
1.405

(It'ic li('n k d , "

C,d"i«C,,, I 121 d4

I
-c ' l s C . / : . ,

C „ A i C n

117.65
I 2 I . 4 I

• Dd'i vdi hop cli.'il pira/.oliii (III) eOn;', hang cAu hinh ldi uu 111,^ vA 111,,. Cac tiiong siVcln lici
phucrng phap iinh hrcrng tir va ioi un hoa hinli ciia su linh loan cho cae dang (leii duac ninh 
hoc nliu IrCn cluing ioi da nhAn duoc hai dang hay d hang 3A vA 3B.

w . ( , >

\ut^

H V-- V i l

: N \ 11

. - - d ^ ' l l

/ /
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k. N — 1 !
-<n/'

I

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N-(MIA)

(• ) , 11

3-+ NAng lirang tong,:

-116654.21 18558 kcaI/m-1
+ Nang luong lien k(d:

-6276,05(11398 kcal/nud
+,Nhiet tao thanii:

98,6418602 kcal/mol

(• Nam.' Iuong tOng:

-i 16653,9403802 kcal/mol
i- "dnt;' lucJiig liCn kc':

•(.3.75,786632 kral/mol
I N h i d liio thanh:

( \ i ' ' > ' ' ^ ' ' ' ^ - > ' - f > ' ' ' '

V < ^ , 7 1 .•>-)->.'0 M . n / i n i >\

MAldddieii n'th

1 c ,

Q

c,

Q
Q

c,

j3dl_

0,084
-0,082
-03)90
d},07')
-O.kL^
-0,01 1
-0,09;.
0,1 a'>
-0,216

lid/iy JA: Kei i|n.i inili lirunp, iir nho dang 111^

)OdAi heu k d , A j d 6 c Iicn k c l , "

CAT 
C . - d .
C, ( ) ,

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(1, II,

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l,d06

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108.41

119.15 I I I | 0 , C i ( ;

Goc lech (nhi dien),"

3,76

i\,('X\ I 130,31 
I J O I I ( d '-,' ',. I I l'kvl''>
I. to I j ( ',().( \„ I 1 I S.66 
i , d ! 7 i ( \ C 3 3 ! I W d
|,"r/d ! C , ( d - 7 I 1 19.97
i) 'en ( d d

C.^i'-S 7d

d,„();C,,d.,

c\c..c,c.

c , c , ( d

17,5t
72,61

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(76)<div class='page_container' data-page=76>

M ^ t (Id (hen ti'ch
C|^j

C,5

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* *

Kft't qtia h'nii hrong n'r va l d i uu lu ..i h i n h hoc ( \'>ny U inh nay diroe hodn ihdnli vdi sif yiiip

b Utn c h o IhA'y, phAn nr i n t l o l y l p m i / o h n (11!) do i ua Chuany tiinh ny.lucn i uu Hiou lux ca

k h d n g eon d . ^ i g phAng va k h d n g con he hen hdu irony Idih vifr Khan hoc Uf nhicn.

hop n o n g loan phAn lir. f ) i e u nay h i . m m.di phii

h a p vdi kc\ (pia nghiii'n t I'ni ph(i n'r ng(paj ciia 116 i';^] f j p u 1 [ p , \ \ i K H A O

I'f^'l' 1 11 AM '• '^M^'y^" M i n h d'li;io, Pham Van Phong.

knycM tap cae h.'\n e;i(. khoa l u K ciia

,,: , 1 - 1 , 1 d i u o n i : Oai hoc khoa hoc l u nhien. O l I O O
Mang p l i i u ' n g phap I i n h loan liu.i lUdn', in , , . . , '• , : " i / „ „ L . , ,
. ,.. ^ \ . ,Ty, ' , , , . , . l l a N o i thang I 1 n.iin 2000. i i a n p d . M . 
va tdl irit hoa Innh hoc ( p h u o n g j.h.ip A M , ) da

xac d i n h diroe mAt d d d i e n n'eh tren cac nguyen -• Nguyen M i n h d'hao, Pham Van Phong, d a p
t u . d d d a i va gdc lien k e i . g t k ICch, nang hrong chf I[(')a h p c , d ' . d(k sd I . d V d ^ - L l (2fK)2).

{6ng, nAng h ^ / n g l i e n kel vA can Innh hen v u n g 3. Nguycai Oinh d'liAnh, NgiiyOn M i n h 'Iliao,

cua xeton u , | V k h O n g no (san phani npirnp, in l a p ehi I Itia hoc. d d t 7 . sd d, dV. 20 (1999).
cua .>-axclyIogicnoI vui t-loniN I n u d I 1 . u n g ., pa,,, N . o c d Inein. I n v e n lap c n hao cao
n h u mdt vAi san phAm c h u y e n ho.i . na 116 (lurp , . , j , , . , ,,^^^. ^,-,.j 'p,.,f-f„^ | ) . „ p,,^. K , , ^ , „ ii,,^, ^ f
cha't dU(/ng nr l l a v t i n va hup chat lo.n n l n c n , OI K^C 1 la N61, ihang d nam 1998.
i n d o l y l p i i a / o l i n iU(nij.' irnp,) j y /_, p

{Tie}) theo ti iiny 12)

ANTRAQUINON TL/ LA CAY MUONG TRAU CASSIA ALATA L.;

CAESALPINIACEAE

I A I L l A l d l l l A M K I k d ) k ,M L. V i l l a i u y a . I'.. I V i n a l Sanlos. Asian .k
u l P h a i m , , \ d d d, No. I. P, 10 - 2d (197(.},
1. N g u y e n Ng(.ic .Suong. Iloanv, Oinh L i n h . .p N g n v e i i \ ' . n i O.ni. Ngn>'en Viel I n n .

d'liai V a n N a m . liai p,iri danv l u ' i i d a[) d n Plinung phap nghien cini cAy ihndc, Nha
Uda luH' Ihang 12/2000. xn;ii ILm Y h o e . d d 2d2 (I98.S).

2. Sedal I n n e iind N a d u l l n / n k l i m l n i . y |' ^ . r d l d a . L, C h n i , d d M n i i ) n i . d'. O k i l d . i , 
[ ^ h y l o e h c m i s l i y , V o l . k l . L . " d O .> t I I f h e m . .•ind P l i a i i n . P u l l , V o l . M^ No. 8

( 1 9 7 5 ) . ( 1 9 9 8 ) .

</div>
(79)<div class='page_container' data-page=79>

TRUNG TAM KHOA HOC TU NHIEN VA CONG NGHE QUOC GIA

NATIONAL CENTRE FOR NATURAL SCIENCE AND TECHNOLOGY OF VIETNAM

40 NAM TAP CHI HOA

Hpc

1962 - 20G2

.

H'l

2002

</div>
(80)<div class='page_container' data-page=80>

Tap chi Hint hoe, T. 40, .so . . Tr. 43 - 46. 2002

TONG HOP VA CHUYEN HOA CAC HOP CHAT Tl/ONG TL/

KHANCON CO CHL/A VONG FURAN

XII. I6HG HOP VA CHUYEN HOA A/)(!)T SO XETON U,O-KH6NG NO, DI TU" AXIT

DEHIDROAXETIC VA CAC FURFURAL

\ ' Dcnion \Oiin H) S 2001

;' NCiUYLN M I N I ! d d l A O , N d U V L N V A N N A . M , P i l A M V A N IMIONd
Khoa Uda lux , It udiiy Dni hoc Khoa hoc 'I'if nhicn - DHQGHN

, ' SMMM.APV

Hy condcnstnion <ij tlchxdi om tin nt ul w nh Im lui olrs llu- .series t>f tr. /l-iin.siniirnlnl I. clinics 
contoininy fiiranc rini:.s lunu- hccn prcpnicl. nhuh hove hccn ihhydioycinnctl to the 
corrv.spoiuliny oiudoys t>f Ihnu'tic in i,\uhly icici wiih phciivlhvthii.inr to yivc hvilrar.oiic 
derivatives ol pyni.udinc rin\;.s.

The sirnetiirc ojproilncts wn.s Uclciinincd hv IK- nnd 11\' .spcclro.scopic.s.

Trong Ihuc le nhieu hitp ch.ii t'hn,i \un-'
ftll'ltn (IA IA nhung ihnoe chua \K;\\\\ h<>.i, I.i 
flht'fng khang sinh dung irong hnh vac ihn y. 
Cung dircc bie't ciic lu/p chat thupc lo.ii .VCIMH (/,
P-khdng no, cAc hop cliAi tU(aig nr Il.i\'oii \,i
cac hop chA't chira vidng pira/.olin eung ihuun;'
1^ cdc hop chAl cd hoat luih sinh hoc ve nhien

11,1 \ \\. ' I . i i u n i ' , t Onj', I l l n h hii^Mi l.n « h n n i ' lOi

il.i lonp hup niui so xelon u.ILkhOng no lir cac
tuilnial \'a a.Ml dehidioaxehc r6'\ chuye'n hda 
I hung lhanh t .ie lufp dial tirong tu llavon hoac
c;ic dan xnal pii.i/olni e('f dura vonp, Iniaii.

(,)n.i iiinh long hop din/e Irinh hav Iheo sO
mat. VI vAy dc? n(}'p tuc nghien cuu iheo hunuy do ph.in mip dir(fi day:

('I

. ( • ( K l i , ,.(.•! X 11 ^ ^ C l K " ^ ,

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.S) p - ( i c j k ; (A NO,; d Li; :d k

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I.

C i i n g ul ^ .u \^ i.i.i .. j , j.i.v,,, M,. ,, n,,,_
c h i i n g KM l h u - hien |)han imp, ( o n - hop d . u : '
v 6 n ^ d e h i n i t laia voi p h e n y l h i d r . i / i n dn nlian

d t r n C C i i c d . i n • . U A I IU.UA.-.-D > n , : . .'.-, ; ; , , ; i , I; ;i

ki^u iii:ylj i:.: :.:l ' \' . • ^ ••

scum (i.P'-d';..diL: n*' \^•^i p u v n - n n . ; , .., t

Ic pIiAu l u g a m 1 : 2 . do v.iy ph.ni nn;.' U r n
nllOin c.iehunyl l i m i hop NC d.ni IMI MI i,ii. \\n>.:' 
p i r a / . o l m ; ( o n ph.in irng n n n n h o M I , U I M > [ | \ |
hiclon ( l r o n g s o n g ) tiAn n u su i.io (h.inli dcx\: 
XUA'l p h e n y l I n d r a / o n h i n h i h u i d i p . I )ieu uav
(hfOc ehihij', m i n h ln!-n plui lionp n n i u i \',i nV
n g o a i . C h a n g han. tren ph<i lioiip, niM^n d.i mai
d i ca hai \'ach dac l r u n g d i o dao d u n ; ' ho.i i n
Clia li:ii l(tai IIIK'HII c ; i e h o n \ I .su '..ii pho eii,i

x c l o n (/.(i-klKuip. no k i n d d,iu. d n'li pho iiV
ngoai da ,\u.il hien Ihem * .le cue dA\. d.u hiel 
cue dai l r o n g \'iing siiii)' d.d (.i.So ^o.| |,||])_
(lAe lump, i h o n l u n n |)lit'nvlhid|-.i/oii Inni hop
(so V(A pho nr np.oai c lia i .\c j i n . i / o l i i i inoup i n 
e<'> Iroii)', lin heu lli;nii Idiao ( y d k N d " ' " i-' d '
c)lia phan i n h d n i h luirn)* i n i o ( u n r -..n iili.in
d i e n nay. ( ac so ln;ii ve l o n j ' hop d,iv i n i a / o h n
duoc gif'/i l i n e d iV hang k

De .\cm \ e l hoai l m h sinh hoc, < hnnp loi il,i
l h u ng.hiem ho,M l u i h d i . i n ; ' . M U M M \ OI . ,i,
clu'ing loai ,V, nm cii.\ l in . ,iii '. ,ni:' j .

p.senilonionos ( k h n a n gAy inn \ ; n i h ) , \iihiili\ \A

c h 6 n g nAm ,\//'/( .///('!///.//(/</dm \'oi ."^ hop ( l u i
dAy lutrng nr Idavon ( I V , . 4. K c i iin;i i ho ilia\' 
ea nAm larp chai ii.iy den c('» ho;ii i i n h chonp,
iiA'in, nhirnj', ehi ci'i .i lu/p ehal co |,h,i naiip
k h a n g e;ic lo;u Idniaii khiit nhan: ( A t hop ( d u l
IVs vA I \ d eo kh;i nang khan;', khn,ni .V nii!cii\ 
vA .suhlilis \'oi m u c n u n g h i n h 2. noin' d^^ A.2"^ 
0,5 m g / m k ( d u chai 1V„ ( , \ la i \ ( ) . i , hi ldKin;i
k h u a n S. nmcus \n\ nine Idi.i t . i o i d n o n i : Kmh 
v o n g Iron kh.inj', k h u a n ki L i m i n i .

I I l D d N f d l l J ' . M

.Sac k y hau iin'mr. d\U^^ nen lianli '-01 |i:in

nUMlg .SIIK ,i;.nd. he <liin;', i n o i n l \ I ,iM'l,tl
c l o r o l o m h.ni!.' 1 : 2 I'ho hon,- i i r o . n d n o r y\\\ 
d u o i dang ep \ ' i " n vin K L i l u ' n m.i . ' . i ^ o | . i
A v a l a i ' M)0> k d ' l l d I'ho i n ni'o.n y\\\ ' i o n : - d i m : ' 
i n 6 l c l a n o l l ' ' - i ! ':M.V l ' ^ ' > f " i !'^ d n m . i d / i i
t h u hoai l i n k l.han.e khnan \A , h ' l i , ' n un d i i 
-ihUc Inen o henh \ u. n l''.^;v

.^^... -iv'iiieinM.VL'h*. 2\,uK ; c n g imj^ in^o 
l ' h ' ' " i i ; ' pk,ip ct'i sail d i ] .S inli(»rni I m a i . .'">
i " l h n ( i i r a ] v,i .Sdiiomlni I m a i ilUf/c IiMif. iKfp
Ld'-. ''•! r'.,r niii(.'phcn_. k v h j o n i [ d ; e i r . ' I . 
5-•- d c.ci [c^ - ^ ; .

r h t n n i g |)h;ip c h u n g n n i g I m p eae M'Inn
• / . ( L k l n n i g n n ( I I I , „)

d n n soi hoi lun snoi .i giid luni hop Id'S
g,!;i, fO.Ol m o l ) axil dclndio.i.\eIic vi'd {),()! m o l
dan Aiiai I i i i r i i i ; i l Iron]' 20 m l d o n d o i n vi'ri sir
(.0 niai cn.i 2 - 3 gi(_il p i p c i i d m lam xiic I;ic. ,S.iu
ph.in i'mg c h o hay hoi Iv'fl dung iiK'ii lio.ic liim
lanh. \AK hiil ke't lu.i tiich 01 \'a kel linh kti lir 
el.iiiol. k r i (pi.i pj(i'i linen n h.ing I.

' r i i u n i i g p h a p c h i m g n n i g I m p eae chaf
l i n n i g (U I d i i v o n ( I V , -,)

l ) n i i .sol h()i Inu siioi S g n / hon hop chii
0,0(12 nii>l \ e l o n (/.|5 klioiip, u\> I'f Indi \a\ O.Ofid

pain (0,0(12 m o l ) luii hip'ith Iionp. 5 m l .xili'ii, 
Lot hill s.iii pliAin liich la va cd ihc kel l m h kii 
IU el,mol. K d (pia dut/c j'.i2/i ihieii O h;inp ^,

' r i n n n i g p l u i p clump, nnip, h o p d a n \ u a l
p h n n h i d i . i / i u i i ii;i K .\c l i n p t Iml Kicn 
I m y l j d i n / o l i i i ( \ , _^)

\)\\\\ sol hoi Inn Mioi o p,io o,0() I mol .\mon

i / . | ' khrmp, no o iKMi V('/i 0,!^ nil p i i c n v H i i d i a / m
\ira e;ii kn V'A 0,.S nil iixil .ixelic diie I i o n j ' .S m l 
I'liiiiok I .nc Inil ,siin phiim liicli ra ('/ ( k i i i j : l m h 
ihe lUiiii tlo \ a m hoiic v.'nij; nh,ii hip,' honji imri.
Kel ipi.i dih'c gin i ' hiing .v

( d//,i; n mil iu)v ih.iiH hn.in llu'iiih v.ii \ii Iw

Ui' i nn chii'ony ninh iiyhicn i un co' hiin liiniy 
hull vuc I Iwn hoc ur nhicn.

L M L I L d d l l l A M K I I A O

I. 2.'p,ii'o.'n .Minh Th.io, I'h;in V,ni ( d . N g u y e n
! l a i Yen. d a p 'Ui ! d . i I".'-. '!', ^^, sO d . 'IV. 
.' ( L ) " : d .

.^ . \ p n \ - i ) M m h 'khiio. N g u y e n krung r i i . m g .
I d m N;:oc Cirimg. l i c e 11 lap e.ic cong
n n d i I loi nphi kho;i hoc \ j i-onp nghe lk'),i

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Anh hucrng cua k i c m tl6'i v o i liAni h a / i i g , chAl Iuong ^A thanh phAn hi'>a hoc cua agar -^*^ 
lif rong C A U cUiVc {(iraeiUnia hclcrnchnlii).

Tlic effect o f a k a l i on y i e l d , t p i a l i l y iind c h c m i c j i l c o m p o s i t i o n o f agar IVoin

Vietnamese Gracihn ia Iwteroehnla.

ic Dinh lluny, Nyd Quoc liUn, Huynh Qnuny Ndny, I^e Lan Anh

T6ng hop vh c l u i y ^ n hoa cac h(;rii eliAl luenig, m kh;incon c('i chi'ra \'.">n)'. luran. 4^ 
XII. l6i\g h(/|) vA ehiiyen IKKI nuM .so \ t i o n i ^ p klmng no, di l u . i \ i i dehidroaxetic va c;ie

fufural.

Synlhesis and t r a n s r o r m a t i o n o f c h i i l c o n c iinalogs couUiining furane rings.

X I I . Synthesis and I i a n s r o r n K i t i o n s o f some (/.p. nnsaiuraled keUmes f i o i u

dehydio-; acetic acid and fnifuialcs.

NyiiY<''n Minh I'luio. Nynyen Vnii Nnni, I'hnin Van Phony

Gic ancaloit cua k\ cAy Mchnlinn.s ohlonyiis (A|XM,yiiace;ij. 4 7

TllC alkaloids f r o ' i i the leaves af Meloilinii.s O/'A'/M,'//.\ (A|XK')'nacea).

i • I.e N}:oc iicn. rhnin Cin Dicn. M. Pid.s

Nghifin Cl'ni sir d u n g cae n g u y e n l o vi Inong, n o n g ipiii i n n h lat* m o i i r n o n g pliiil n i e n 5z

vi khiiA'n d6 x u ly n u t k t i n i i .

Study on' (he cffeel o l ' lr;iee elements on the j n o w l h ol mi( l o h ^ in v.'.isiew.iler.

; I'l mil ic lluny^ Nyuven ThiMinh Nyuycl

Zeolit Fe-modeinl: dVing Uap, dac n u n g vA ho.ii ti'nh xiic lac l r o n g phan irng o x i hoa 56

phenol.

I. TOng'h'ltp vA dAe linnp, nii.i I r n i o . K n n

Fc-mordeilile: SynllK.si.s. d i a i . u u n / . i .iml ,i^ i n i l y on lIu- o s ) . l . i I i o n ok phenol.

l.'ITlC synthesis and c h i i i a c l c n / i i h o n ol L c - m o i d e n i u - .

H • ' . Dnny'l'uvcl riuiony. \'uniir Cm Tlu'nih. Nyuven I luu ihu

T6ng hap cac dAn xuAl nuVi e(') c l i i i i i u i u r e u . i L d l e o \ o i n l e i n i ' . i n i n . h2

Synthesis o f new n i l r o g e n - c o n u n n i n g l2-di.-o,\o,n lemi.sinuMka ivnlics.

'll nn Van Siniv. I'in/i Ishnc \'u. Nvuv<-n \'nn 'I'uyen

Hal hop chA't a n l h r a t p i i n o u l u cily L u o i ran [llcdvofi.s Ciuvniho.sn) v.i L u o i (An Irang

[Hedyotis diffifsa).

Twoanlhraquinoiies htmi lledyolis coivnhos.i .md llalvolis diflusn.

\ ' , /..// Kim Duny. I'om \'nn Smiy. I'hnni Cin Diim

tec diiu n g h i 6 n cdu w i h i i i i h plum ho.i luu- ^ iiy hn u.\ .scmi, ordnui. 
SlUtly on the c h c m i c i d con.slilncuiN id' /-V, //,-, .scum mdnln.

Ni-tivcn Vnn l uycii. ldm Vnii '.'.uny. Nynyen Mniih CiU/iiy. 
Nvuven lU'ch 'I'lnu'm. Nyuven 'I'lii Ihnih

fe

\^a\^ chA'l i u d o h . p y i i d o . p n n a . o h n a i u - i k - n u. . ,is I n d u - ka ( / . r / i d m / n

hotomum L o i n . ) cn.i Vipt N i i m .

i c e i n d o l o p y n i l o c p . m a / o l i n c i d k a l o i d s l , o m ' / e / n d n ' / m truholonumi L o u r . 
(rowing in V i e t n a m .

Bid Kim Anh. ToniWrn .Suny. Nyiivrn Manh fnidny. Dimmn'e'h Tudn

(•)(]

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(85)<div class='page_container' data-page=85>

TRUNG TAM KHOA HOC TU NHIEN v A CONG NGHE QUOC GIA

NATIONAL CENTRE FOR NATURAL SCIENCE AND TECHNOLOGY OF VIETNAM

T.41 2003

</div>
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Tap clu lloa hoe, 7". 4T so I, Tr. 51 - 65, 2003

^

TONG HOP VA CHUYEN HOA CAC HOP CHAT TL/ONG TL/

! KHANCON CO CHU'A VONG INDOL

Xni - TONG HOP VA CHUYEN HOA MOT SO XETON ct,(3-KH6NG NO 01 TLf D A N

' XUAT CUA HIDROQUINON VA CAC INDOL-S-ANDEHIT

\ Den Ion .\onii I/ / 2002

N G U Y A N M I N i n i l A O , LIIAM V A N PIIONCk liUI M A N I L k U N G , V 
'irudny Dni hoc Khon hoc tif nhicn. DIKXJ Hd Noi

MINI! MAI

S U M M A R Y

Some (r.fltui.snfiirnled kcione.s luivc hccn prcpnred hy (he coiidcii.sdtifxi of 2 
ixclvl-1.-1-dihydrovyheno'nc. ihc product oJ h'l ic\ icm mnyenicnl rcnelion of hydror/uinony! tluu ciile. willi 
wdole-.^'Uhlchyilcs, \vhi(li tunc han inin.sfoiincd iuli' iCirespniidin\^ Ihivnnc iiixdoy.s or 
imlolyl'pyrn.'iiliiu-.s.

Thi; slruclure of ihc.sc proiluels hnvc hccn dcicr/nincd hy IR, IIV and 11-NMR 
spectroscopics.

Trong mpl loai cac c{"mg ninh irnor d;i\- 1 I .S| C.'::, ; loi da Ilu'mg k.io \ e sir I,^ng Iiop \'A
chuyi^n hoa cac xcion o,)Lkh(')ng no di iir d.ni xiiai ciiii m'sMophcnol va cac indol-3-imdehit. 0 hAi
bao nAy chung toi dA thirc hien M; ion;.' hop \,i d m y c n h2»;i iir(Tnp nr nhirnj', di lu d,in xuA't cna
hidrftqiiinoii.

D ^ CO chA'l dAu, clu'ing KM da csle luiii hidrofpiinou \'i"i ihirc liidi phiin ung chir'cii vi k'rics
11(5 lhanh 2-axelyl I ,d-diIiidroxihcn/en ((piiniixelopheiioii).

Oil

( ) C ( ) ( d l ,

Oil

'OCH

I- ( C I ! i C ( ) ) d )

AlCL,

r.o- ir,.'^"(

o

OH

( ) ( d ) c i i (

( J l !

San pIlAm eliuyen \i Liie.s n,-i\' l o ninei ilo \M \,idi d.\e iiimr, eho (l;io dOii)' Ww tii c\\.\ 
ming chay phi't hop vnx nlnei dn nonp, di,i\' nhom ( < ' o I {)d() e n d (nen pluS csle o siV soil]-, 
^rong tai lien iham khao |(>k Kei tiiia phAn iich c.u) hon v kien ph(d(^ng Iiirdig lu jiroion cua san

nguyCn \6 ciAng phh hop voi cnuy llnre ihr kien. phiim dni'/en vi Liier lIiA'y xuA't hieu cac tfn luCu 
TrCn ph(5 hAng ngoai IhAy xmli hien \ a c h d.w. cliuydi dich lu')a hoc cua cac proton san dAy (cS, 
irUng cho dao dt'^ng h()ii lij eiiii nlndii O i l ppm): 2,28 (COCI I,); 7.13 (ILC,); 7,00 ( I L d \ ) ;
phenol a 3248 c m ' (o phi'i eua diesie kli<Mir, ( o) 7,2() (I k ( . d ; ^'.•'^" ^'i 7.61 (cac nln'mi O i l ) .

</div>
(87)<div class='page_container' data-page=87>

/ "

'lir san i)hAVn phAn i'rng chuyCn vi Lrie. a nhAn ducic m6t day .xcion a.P-khAng no r6i 
tren ehiing toi da cho ngimg Ui v6i ciic iiidoLd- chiiydi iiua liO'p theo tiiAnh -iic hop ch.fl tuang
andehit lrong didu kiCn eua phan ung (daisen - n; Oavop. co chua v6ng indol hoAc'cdc hop cliA't
Smith (niAi inf{>ng kidm manh trong enmol) u^ kidu indolylpizazolin theo so 66 du6\ day:

Ol!

CQ:

Oil

:ocn,

'*"

-^ imi-tdio ^ ' ! ' : v (Q

COCIl--Cll-lnd

Ol-.'^) 01 P d

(yii.,NjiiNii
>' 01!

IIHI

I I Jl

(IV|.s)
(\.\\

on

a dAy: Ind " I) Indolyl-d; 2) 2 iii(iyIindoIyl-3; 3) 2-j>h'.iiylin(IolyI-3; 
d) N n n c t y l i n d o l y l d ; 5) N iKn/yliiidolyl \

Cac xclon (/.,|LkIi(^ng, no duac n m h hay (V tin liUig c.'m Inic ph.'in liV cna e.ic xclon a,\\ • 
hang I. , klK">ng no iih.'ln duoc la diing. Ngoai ra su li'nh
. , . / , , . • , , ,1 lo.ui lii'ia lirong tu vd su iihAn IK"^' (hd'^n li'eli ueii

I rCn pho houg imoiu i n.i e.n v. ion od^ . ' .

, , „ ,-• , ,1 I I . r.K ni'UN'i n nr emm cho ili.'lv cAii liam; t'"^! irn IA
khOng no den Ihav Miiii hum eae \,i. h d,i» lump. ' •' , . • ^. , • ' , , i - : d

, V , , ." . . , .,, /;,.•/.'. \,i phiin IU giin phani;. he liOn Imp Utn^e
cho dao don:.', lioii in cmi ciic nhom ( )l i iioin' ,, ,. . '. , . ^ ',.. ' • , ' .•

•^,^'2 'v^nr^ I • I - /Y^ I I , I' ''' 'ku \'.i (lo duom; dien ucu cac nguyen nr 
vung 3 6 / - . 0 2 0 cm , cuii nhom ( O hen l](/p , , . .; • , , , - /o m o i ^M^ 
^ , , , ,,, ,^ ,„ ., ., , • hi'no cua nhom vmyl klui ciio (0,132 - 0,LM))
trong vung 1618 d 6 4 8 cm Ngoiu la nen pho , , . . ,, , , . > ,A ,i

' r-. , - 1 1 - , , 1 I lAno Ki-M. do (() Ciic xelon a,\\-k\\U\\v no nay dt Ih;im gia 
con xuAl luen vach dac lrung cho (kio dong hien , ^ ' , , , , i ,^ , / 
dang hA'i do'i xung cna nld.m /nm.v-vuiyl o OdO - ^'^^" k''^"^ ^^"^ '^^'^'^''-^ ''^''^ ''"'^t'. vong lhanh c k

1006 cm ' va dao d()iig lio;i n, cmi Nd I mdol o "^'^'^•" "^^'"^ '^"^'

3 1 0 7 - 3 1 7 2 cm k k.Vic lu/p cliAl lU(;iig nr lliivon (Hi,.,; nlhln
,^, . , ,1 I 1 - difov hanu phiin t'rng dchidro luiii dt'iiig \'0\\v cAc 
Pho nr ngoiii CIKI cae xenlon (/..iLkhong no • ' , .. , , - . ,k , • .
. . . . e -• , , ,i.,.- , , a, . ; I xelon ex. i-khonc no hoi luu huynh. S,in pIiAm o 
ghi trong cac dung moj clanol thuong d i o .^ - d d , .- ^, , .^ _ , -^ , , 2 ., .
^ , • r V I , - - -ino o-)i -'s7 ^^'^^^^'-^ H'lh Ihc. CO nhi^i dO nong chay va gia tn 
circ dai liAp Ihn trong eae vnng 201' - 21.-. -.^/ - - - , . , , C , , , ,. d

261 -^76 ^ ^.S.S va 306 - d l 2 nm NO, \\C SO lai l^i 'i^^'i •^•'^' ^-' '^^^'^ '^i^^'H^. khac yoi cac xeton a,\S 
. . . , . , , ,, ; , , ' o.ciM' no kln'/i (k'in. dren plir> liAni; iii',o;u cna 
phAn liriu<rm'doi km lgi: - k*d -IJ A. _ • . , , , . , i IA 
' ' .• t^ d i u n g dOn co c;ic viich dac iiiriig cho dao (!()ng

l>ji6 C(.^ng hU(Vng iir pn)ion eua moi hong ho,, ni cmi nhc^m cachonyl Hong khoang 1 6 1 8
-cac xcion (/.|i -khOnj!, no (In/p cha: I!,) d : o ihay j , , . p | ^,,i'i. ^^.^^•^ uhAiu OM (V 3167 - 3259 cm'', 
chuyen di(li ht'>ii h>'C 1 li.i Ciie piolon nhir Siin ' o . ,.,1^, jdn'in-i iNd I ind(d ('r 1211 - 1247 cm"k cmi
ppm): 6,8(1 111 ( d . /.ill \.i I.eo , ! ! ( ' , \.i I! nlio;n ele \("Mig (V I 1 32 I 1 76. PhO li'r ngoiii ct'i 
CA); 7,4'-' ^'il 'k'^^ (ear j)iolon ' ii.i nhoni i: .no. kh. MU:' d t ire diii hiip ihn lioni- vAng. 2lK^ '• 222; 
vinvi}''7,23 - 7.31 C-ie piouai cuii v>^\\r. indoh; .pp--, - 25A. 266 - 303 w'l 303 - d l 2 nm. Cac du 
8 10 vA ^kL" (•. .IC jiroion tai,! . ,11-idioni ( d !). ; ;,'.i [di'i n.^iy, cdng xni kei (piA plt.di tfch

</div>
(88)<div class='page_container' data-page=88>

/

PT-o 
a 
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(90)<div class='page_container' data-page=90>

2. PliiraiiK |>h:i|> elmiij; loiij; hop c;ie xt'tnii d6np j)hAn u'r yam eini xclon (/..|i-kh6n); no va

' a,0-kh6ii^ 114) (II,.s) phenylhidiii/in troii)^ cl;inol V('ri v.ii pjo( iixil

• . axclic dac lAni xi'ic liic. San pliAm

Nh6 tir nr lung giot 10 ml dung did. Na(J 1 i„^,^, , i,,,,^ii„ (.-,,1^,., ^,,, .j,^,^ ,\,^ ,^,,^, ,^,

.^60% vao |i6n hup cna 0.01 mol 2-axetyl-l 4- ,^,.,, ^. ^,^ ^^j^^.^ .^ j , , ^ ^ ^ ^ ^ ^l,. ,... ,-^,^^^-^^.

^/dlhldroxibcnzcn va 0.01 inol MKk)l-3 andclul ,,},-,; ,|,i(.inVp;,„, 3,

trong 20 ml clanol vai sir kliiiiVy in)n niiuih vA

\hm lanh hen ilj-oAi liAng nuoc dii. De ven luai Cony ninh nay duoc hodn ihnnh voi .siiyiup

hop phan irng o nhiet dd phong suol 1 2() gio. j^y ^,^,j, '^.y,, ^.^^^^ chiumy ninh nyhl2n cdu Khon

Sau 66 pha loang bang 30 ml nuac rOi lump hoa ;,^,^.,.,,/,,//, f,.,,,,,, u,,/, y,f,. A'/OM //n« n/iduni.

' bang lircrng axil axclic tliroc iinh san (inoiip,

duang v6i Iuong ki^dn da su dnnjO cho den moi ^ ^^1 I l|-,.j, ' m ^ ^ i j ^ | p \ ( )

' lru6ng tiling ifnh, san pliAiii 6 dang kei linh

duoc tach riCng la, loc hul lU.i l)i|ng niroc , de , pjj.„yO„ Mn.h dliAo vA cac cong sir. dap cin'

khd ngoai kh6ng khi vA c6 the kei liiili kn in Ihki hoc, k. 35. s6 3, dr. 17(1W7).

. h6n hap etanol ; nuiVc = I : 1. . K, - »,- . ,i • i„ v,- ,- M ^

: •* .'. Ngnven Mmh Hiiio. Phan Van ( u. Np.nyOn

Ke'l qua duac limh hAy a bang I. Ip- 'y^;.,, p-ij, ^p,- j p^., j^,;^.^ p u,_ ^cV .1, kr.

D / 1 0 (

{199S)

3. Pliin/nj; pluip ehiing long hup e/n eluK

lucmg lirllavon (ril,.s) 3. Nguyen Minh dluio, NguyOn dim I.itii.

D.Uii- ()u6c dhiuih, Phan VAu C'lr. d"ap chi

Dun sfti hOi hru h6n hap 0,001 mol xcion ^ j^, ,^ |^^-^ .j, -^.^^ ^^. j .j.^. •y2(\^)^y)).

a,[3-khOng no vai O.OOI mol lun huynh

IK.U)',

.S ^ \ , , '

-" 01 \ / . r.i .

n ; i x i l c n M i 6 l 5 - 8 g . a . S ; m p l i A n . d u a c k n l i . a 6 l- Ngiprn Mmh Ihi.o. khau, V;ln I ho

,rang thai linh iU6 duac hut loc va dO kho m-om f^'y^^" '^l> ' ^''^ ^^"^ ' 7 ' ' ^;''^.'^' ''^'^ "^^'

k h A k h h c 6 llie kei linh lai IU 1.611 hop mamd jnd;. _ f[.^^ 1

'M J ^ ! ; ; ; ' ' ^ . ; : ; \ . : T ; ;

• " ' ^ ^ ^ ~ ' • ' - n i l p H d I N I k i N O i . l i . 1 IS ( . ' ( ' D M

'n Ngn)'eu Minh dhao, Ngnycii Dmh DOng.

Ke'l qua <luac p.nn Ihien (V h.nii

Phirang phap cluing (oi

indolylpira/.ohin (IV,,)

Dun sOi li6i luu .sum 5 - 10 gi«f hon hup (he lliird cdilion, Longmans. P. 667 (1%7).

4. Phirang phap cluing (<Mtg Iiop cac p;,!, (hi i p-i.i hoc. T. 39, so 2. d'r. 50 (2001)

indolylpira/.ohin (IV,.5) ^^ ,^^ p Vojud. Piiiciiciil orpiinie cheiiiisiiy

</div>
(91)<div class='page_container' data-page=91>

^

8 Biin vC mO hinh loan h o c ci'i.t l.inp kiipni;' \;i l..ns olol i'^.i!sM)n sU dimp <iien Uifdnp 3d

de* xac d i n h n h a n h d o khiieLl. i.iii ion ( I nnn;> IK-IOII;'.

T h e malhcniiilieal m o d e l ol d a n g Liij)in}! iind l.ais olok Niison iipplicd an cIcLlriciil
ii field on rapid d c l e n n i n a l i o n ok ion CA (iillusion ii. c o n c i d c .

I'hiin I'd// Tid'Hi;. Duny Ihn; 1 'dn. I'rdn Dinxiy

9 Nghien ei'rii khii naiip h a o \c LIHIIIJ- an iiuoi l i n i inai i I o p * :K hon i u;i m.inp phii lu'n 3 / 
CO SCf p o l y m e iiciykil Um ironj' nirik co rjnoi phniphoiiiii linii ci'.

Sludy on ihc e m u l s i o n polyiiH-M.siilion nl niDnninci-^ jciykil'.- '.villi Ihc presence ol

organic p h o s p h a l lor p i o l c c l i v e coaling' ol t . n h o n '.leek

11 inh Anh 'I t lu

10 Urig dw'i}^ hhih hoc pli;in hinh m o pho np t|n;i n i n h polvine IK'HI. ' 1

-; Fraclal g c o m e l r y applied lo snniikilion nl pok, H K I isiUton pioci"-;.'..

/ /' l\ini I oiif, I run ;Vi;o( I'liicni. \'Ci Ih'nni Sinh

I I • T d n g h o p va diinh pi.i lmh chai en.i nlin.i ' nn, k'-.U' lieii v o ,si'' II.IM .I.m n.uih epov;- lin.i -IS
(BSO) v('/i axi! meiiKivlit

Synlhesis and s l n d y on j)M>petlu's ..1 \'invk".I.-i irMn li.r.e^l ' N rpn\idi,'i-(I soyheiui 'ol
; (BSO) and m e l h a d y l i c iieid.

i Nyio-en llnn Nieu. Nr^uvrn Ihn Ihnnh. Ln'I'hni I hi

12;T6ng h o p va r.glm'm ciru khii iiimi' hiVp plm ^d ' noi n'^ll siii.
, Synlhesis ami simly on iidsoi piion N r ' nl n o n o.vide,

/ , \ , , / / i \<i. ! c lhu n.-m:

13 TOng h o p vA clm)'e'n ho.i c\c | i o | . ( h.n nion;' m kli.uh on i M , |i;i,i .mi;' iihlnl ''I 
/ H I - d"6ng h o p v.l ( I m y e n hn.i mm , i •.••mn '.-.i'. khioiy n • di m d.in .MMI ^ UA

hidr6qiiiiion vi'i c a c n i d o l - 3 inuiehi!

Synthesis and liiurdoiin.Uiiin old hah IMM- a i n i o : - . , niil.ninn;' indMJ.- i ni;"..

Ill - S y n l h e s i s and iiansrorniiUion i.id.niiir o . j ; im „mmi!rd I -((.m-. I m m d n r . i i l i w . M|
h y d r o q u i n o n e and iiiclole-3-ini(k-hydes.

Nvnveii Minh 'I'lidn'. I'hmii \ mi rh-'ir.;. Um M.nihl nn:;. I'hri'hl Mndmhn

14 N g h i e n ei'rii dn hk'ii .in m d n MLI h./p Kim I'^an- |>h.uMi;' ph.^p i>!in mm- im 4uA\ Ima

(1-kS).

Phan 1 - P h o UMU' u 6 ^ iki lop plm Imp kim / n No

Study on Ihe \ o i i n s i o n O'sra.nKv nl .,I!nv hv I ' l c M n . h e m o al h n [ v d a n a
-Spcctrosco|)y (kd.di niellmd,

* - • ,,,-, .mdv -1 /iiK 111 k-I ' n,mii)v

Par! I - I d e c l M K h e n m al Inipe.kni' <• >|i> • n

Sro (iu.''e i hiveii. N}:iivn Ihi (yuMih Aiiii eh.nn i I me.

5'\

nc

15 K l i a o s i i l s u l u r n d n m a i i l M . i emi almnai • ho a • „ l-aim phnmm |,h,i,i plm Imnr n;M u , 12 
vA pho liV iipn.n.

Sllidv on Ihe snumiiM' e h a n r - . •'! i i i - l ^ ' ^ ' - - ' ''k'in-M>' I'v .nlian .1 I IK) and nllia v m i n
( U V ) s p e c l r i i ,

hern- lie ILmh. N:-i\en (Jmu Ihen

</div>
(92)<div class='page_container' data-page=92>

Tm<: oiiAN'iaiM ('Ai.( i i i A r r N n Ari-MCAiioN IN i'im;s

RKARKAN(;i-;rUJ';N ! O F RI'SORC INOL DIACKIA I'lO

iVynyi'ii .Minh Ihao, l*hatn Win Khony

lliiiioi I 'iiivii wily i>J Sciences \.\'l'

\- m:nk ph,inrw,n_ pfn m"''p \ahno.co/ii

! ; n M M M , ' \ ! « ' \ '

T h e I'Vies rearrinigemeiil :d ic-,>m. imd diicci.im ' d \ n s m o m ilmn o n e prodiicl, I'lic rcsiill ol'
this rcaclit)ll \N';IS sliowctl w l n n 1 \\\'.)\^ id i C M m m n l .ii--(,m' i c . o i c i l wilh .^ midc;: n\ ;ilmmniim 
chlorides:

Rcaclioii ill IdO- IdS'V 2 iciiH cinplirii<me (.'d',; p and 2, 4 (hiicel)'licsoieinol ('kS';;-). 
RciiClioii ill I .SO- I .S:V'( ': ir-,n' elMplmnnm- ( W'.di. ,;nd ', I ihiieclylresorenml (60'','d.
R e a c l i o n ;il 2 0 5 - •21ij'V2 ic:,,h ru .phrnnim ( / ' i ;, '. I di.mciyliCMM-miiol ('kS'/J, mid d,
6-diacelylrc.sarciiiol ( kl'.'n).

Mowcx't'i", hnili Ihc prelcfiildc loi mainMi ok 2, d • dmcep, Iresorcinol mid Ihc I'ofmaliens of ihc
oilier rcarranp.ed p r o d u c l s lm\'c no! Iiern clc.n ly c.\jiki;iimk lic.sidc-s rc-cxiiimnin:.', iho.sc resulls l)\'
doing CXpcriincilIs, we lm\'c im^'d . \ l \ I I )|ii inlnm n i r l l " d k M r,ik'i)I:ilmp llu- nmn incdiale pi ndncl-; 
of I Vies rcarrnnp,cincnl ol II':,MM'III. i| di.D nUl,' in n •, pkun l!o lo-nd ol Ilns r r n c l m n . d' he cilciikiled
rcsulks IKIVC md o n l y pio'.'idml ;i •..\\c.\T •: ve (o r \ p k i i ! : ;,.• JniMoniou ok iL'.nj.nip,cd poiducks Inil 
;ilso e n h a n c e d us U) inipi-ove c \ p m ininiiMl , Mmhiion,'mii oidm h. t-kiinn cx[ic(de(I pKulncis

Refereiu'cs

\. Desai R. .S.. Mav.nii (.'. K, ( I ' M " ) , / /. •. . In.! .l< ,;,/ ,v 'nn dV \ 
2..V.V. ' ] V ; i \ ' r n , \'^.\a. r u d l i . i l i i M M , , A . V , T.V .wee.. 2\.\2 i \ i ; i i t ; i r \

Pmid himi <)ol !TIT(.-VTD>.

</div>
(93)<div class='page_container' data-page=93>

' r n i ' ; o i ' A N i ' n M ( ' . w , ( i i ! , . \ ! [ \ n '

A I M M J C A I I O N

i i i n i ' S

iU'iAKK.A.Niii'jMllMOi' R i S O i ^ I N o l , !)I,\Ci. : \ j

,\ i p / v r / / Minh '/'Inn . I'lnini \ nn I'lion

llnimi {hiivcrsil: <»/ ' i c / c / n c.\ \ \ l l

k'. m a i l : ph.me.Mii p!p ' M ' ' ' ' ' \- A\ ' '111

,SI ifvlMiX'kAkV

lln- n.Mny ,'l .\.\l 1 nu-lh.-J !.'i . .1!. n!n:,iiy lln n}l<-i in.-dnn- •".^.hnn .-! / M , ^ 
rmn ranyi'iiieni oj rc.\/n 1 an u' dnu dale Im.: pio\idc(l a .aiiiph civ !>> cxphan ihc 
h n iinil n ni <'/ 1 mn 1 mn'.ci! pi. liln, e

T l i e I'l ics ('-nci m i n t n i e m r d I O M t i e n n 0 1 II,M •, (an- p m e ' . nn -in l l m n m m 1 - Im I d i m m v n l l i d

ihis rciicl i n n ' " \ " n ' >2i' ''^-rd • I m n I m i dn 1 il t n'.' 1 11 m l a^ m .iin 1 r a ' lei I " i l h > "A'-' < •\ . t h n i n n i n n 
tlilo:,dles

• I v c a c l i n n ,11 I h ' 1 I ^'X ' 11 •.,!. o . - p i h n, im ':!' o .111.1 ; , im. . 1 \ l u - , , ^ i-, : - ! ; • . :
• k e a c l i o i l ill INO- I .d'e'( 2 ICS.H nU iph. ih in 1 ^ ^ ' o m i d 2, d- di.im-I v h e v o o i ' H : I ' . i " , I

• R c a t d i o n m . ' i l ' ^ 2 I ()"( 2 i n ' . , i m ' l i i p d - a i ' a i ' . 1 ' ! -ha. nl^do-M u n a : ' k : * o t i l l I '•

idaxetylrcs' )\\\\e4 1 I d'a '.

I I l ) \ \ ' C \ C l . hi i i h i h c p K d o n h I n i; •;;: : , i i ; , ai ' d 2 !• d m . - , : \ I I L ' M u i i i : ' ,M!d !!;•' 11 n '! : ; i ! i-'i I
ol' ihc ( d k t c r i c . u i : n n n - ( ! p i . / i l u e i - . ii.iv i h ; i i K i i i . k . n i x n \ p l , i i t n d I h o - ! M - ; d , . i n

c x a m i n i l i ! ' I l i u s c i n m i l P . I n / l n ! : m > ' . - - . p ' 1 n n . ; d - : , \'.c ! m \ ' c u c i l , \ M ! > f .\\\A'.\A M i c i h ' u i I n r 
c a l c u l a t i l P ' \ne m i M i i u - i I m h - i m I ' l ' i ' !• ' d h i n . o 0 1 . n m n 1 a m i n f i m . . ( i n d < !i;n id ale I n

e x p l a i n ! l m n o n l n l i h i . •.c.\.A'rr i l a : ; d o i h i l n d i n , , i d , : i i s n h.a • n i d r n t a n d i r . I n 
i n i p i o v c c \ p e l II i I' •; ll ,d i > a ,d il n n r.

In,'cn S l i p p i n,cd |. ) ; d h na : i m ' , . - \\--\

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l l r t r t t oi: I n l . a , i t

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>miMl \ ^ d ^ \c\ I " n 111 i l l . a n . n

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h i n i a i i K i I ' l l . , in' 
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li.j o l i n i . p ;

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(97)<div class='page_container' data-page=97>

1 Sonic ( l e d i i i l i n i m w i i l n h i i w i i iVnin ihm.n . dt nkilcd d.il r

• - n i C i n i e n i i e d m l c siihslniuvs Mipp-.and i,, lu' hiMin-d d m i n p dm iv;t. i,.Mi (( I ; I 2. ( hi I d .

(•rr224, ( T V 2 d f O w c u - p k u i c . d i m m n . dm n k n . n n i p l e - n - . hmx'.ecn . • . , ! > . . i n I . n . m , . - .m.i
aluminum alom were nhsciA'm!

- ' i l l e n p u I n l i c s n i . i m d ,||.u . i,in . i , , , ! . . f i n n n i . I i k n u l e is ,in ni ,d. a I i . ' i i i lu pi n. r e d :

Alk= AlKCTr) i .:/\l I K dl,( ( ) ' i ,\l hcsim , .' \ l n \ l ( i j I n' I V i 2 ' I M i ; i i ' ' / m , 2 i

|.|(l.3,^)- 2 X ( ) d i ' ' / o , / / , / / / o / , I IriM c o n Ihn hi ; ' n i n n i p M| i l i r , ,, ,1, i l i m n n v i n , h id n i he h. ,ii.a j

I'AperilllL'lll.'ll .sllnV.'cd 11 ml \ \ l m i l d m i n i i i p n i . m n r i il u ,n [ h O i, n n h ( d : ; [ l " { 2 I n a i m 11 I hk II id) •'. .V.

[I'lLMSed. A k l e r t h i l l , i h c i m n p h - ' . . I n n i m l m n | n m hn,l .,. . o n i p a i i u d h\ lIu- n l l . i nj ,„ r l \ I i n o i p o i

\\e itcnzcno nnc lens.

- l l i e d e l mil V i d ( l i n i p c .11 i h n k'' .111.1 n"' , .1; P. ai , i n . t i i ' . n| iPi ( 'h . , • i,,.!, . , /•/. ' . \ / / j
.,|,-more n c g a l i v e l l m i l l l m l i4 I h c . ' ' " ' n i m f-'^..'•/Ad I h . i n h i n ' . .m n k ' O i n p h i l h ai,,m .d .m ,,. n l \ I 
liilioil in} l l i e h u i l i n i *U]c\ \\ i i i M i c j a . I. n i h i l - h\ i h n I n m l i m i i i n i i n . ' \ ' . 1 c --ell I 
.lU'iylresociiml V'.m.s i h n p m . I n m n m m p i . M Im 1 , ,| d i . ' nn.- .n • ; \ 1 i n . , | 1 nn;.'nd m.i ; a a i

- W h e n 'iiii . M c l \ d j ' i n i i p n. I i r . K ' • i i p p , , . 11 n ) 1 nphii n ,1 ICMIM iiMai ,iln, 1 M ip, ' " ' p. .vip,,!,
11 T r i 2 ) , Ihe n i n i ' e i i c p , i l i v c | \ o h m p m l ,ii i l u 1"' . m d r''' mn hi ,M . i h a n a 1 d l l m . i a n p l n - o 11 ' ' " ) ,||,,|

11,11 ^) is oh.seiA'Cik I n|- i h m i m n t i i o i l i nk m n i p l n h i .ilhu I n i an . n n i \d nnl i m i ^ ai l l a - . n |i. . n ! i. ai-.

111,1V he easier. ,

. S i m i k i r l \ 2 ll ,111 ,!• e m I p | . a i p e ' . i i | | 1 n • 1. p,',> n ,, ll \ d n - • . II . i h a a i P , I"' p> • il i. )|i 
I ' T l h l j , d i e d " ' p n ' n l i- HI ( ' ' i h . I h m 1 a I f • ,, 1 •: • 11- ; o l I . > 1 \ i !;,i( ; ' n . I l i i . 111 (•'" a m 1 ' ' ' ' > ; i j i i m ,

tliu-leophilif re, I. I i \ Us ,il l l m .'''' p. ) M I 1 n )M n In ado l l m i i h ' ' . a m

f i e c a u s c n l i h i i s i ' k n m l i e n l i c i s n i n . , ', 1 d i m el N d i c m nn )I wns . i h ' . i \ ' . a p n ' d n i i i i n , i i i l
|IIIKIIICI o l l l u : n m c l i n i i \','hcn ;iii c,\i ess m n . a n i l n l . i l i i m m n n i 1 I d n i idc WAS U.M d I ;csides, ihc liciil 
iil'lurmnijoii of" i h e ( 'k'r(-2dd m n i p l c K ( w h n h l l m n In 11 m m l n '2 d dl;^'^d^dI•CM > i i i ' d 1 n, Xl(nl dunl 
huvr ihan I hai n l l l m ( d r i a M r l a n n p l c x c d n . h i h c n i m o s m i n I. ^ d i m c l \ d o < 1 n i " ! 1 n n a n P a n .

''Illy wa.s a Slim 11 n n i n m n n l d . r . I n U n m li.".> >. m. 2 Ini n a ' d .il h r d i I.'M ip.'i nl m • r
Hy a n a l y s i n p : I i c C i d n l l k i l c d d . i l n IIK- ^ ' ^ p n M n l n l l ( n l i n i i d i h n i i s I m \ n h.'nii t m j a n \ n d l o

iiiililin ex p e e l e d p r n d m h. N c s n i on i p l u a a 'ii" lar- h- i n n m , 1 0 0 0 ie< MJuni f r ' ' ' , , " Imn l l m )n,iO m n " -' 
I'llipe'raUllv a n d l l m 1.11 m lu-n/.ta-n d m m i n i ,iii,l . i l n m i n n m . hk )i idn l m \ ' n : mmi O'. Im nd 1 I i' 1
kllk(!; 1 n i o l e t d ' l l u - c . i c i : 2 n n d e n l / \ l ( 1, i h n l ihe ie,ii I n m I i i i m 1ms k e e n I n m - l h c i m d ( ; Imn i s ) . 
' *l ' l i a j f e l y l r e s , . , m, .i h.-. a i n m .1 p m . l . u n i i m m pn ^d n o i f- h o \'. hnn d in i n, i. l n •, 0 - . >! pI.i. n ,ii I 7( I

\1S"(\ i h c rai i n h c l v . n n n c l e i .Hid ,iln n i n . h ' n n d n '.' .r, m m d i n . l . ,iilil l l m n,,. n, .n M M I , •• ,r. d

'ntirs, 'Pile l o r n ml i m n - n l llm-.n ptn< h m h . l m \ n hnn n d n h ' n n n md h \ d I N M N s; . n..-., . .ps'

Uy ll.sni): n l / \ M I n m i h . - d h a . nk n k i l m i ' i h i i i i l n m m d m l . - p o u h n Is . >! I 1 ms i n.n 1 , m m ' n m i l l

# . s o r c i l l o i (liiK e l n l m di<- I n n n . i l n w i s n l {\n' p u d n i ; , n m n i p o d i i o s l o w s i m p l \ l-ncii e \ p k n n e d . 
mil the e x p e r i i i u u m l .< a i d i i m m , (i.e. n hn.'o n 1 i p m ' , nd n- , d . o n i n ' . p n o c d p i . ) d n o ' .

(I'ferenfi's;

Ik'sai R. S., M a v i . i i , (• K ( I W - i r , . / , , . h.l \ ad S o n . 2 ' > \ . | r > i ' ) ^ 27 ;

</div>
(98)<div class='page_container' data-page=98>

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- D a n g h i e n c i h i phan u n g c h u y e n v i Fries cac dh\ xiiSft axetal cna m 6 l K6 phenol va 
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phircfng phap l m h hoa l u o n g l u .

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nhau, I m n g d o c o m A l so chAl rAl d a n g c h u f va ciin dutic nghien ci'nj lie^p luc.

K i e n n g h i ve q u i m o v a d o i tircmg a p d u n g n g h i e n c i n i :

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rnOI .so h o p chAl d a n g c h u y ) l A n g h o p d u o c . D o n g lh<ri nghien c u u m o rAng sang f i n h vuc
chong u n g I h u va c h o n g H I V .

l i o l(^n

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<a href=''>L t H . i t -</a>

Nghiên cứu tổng hợp, cấu trúc và hoạt tính sinh học của các hợp chất tương tự Flavon, có chứa nhân dị vòng

<b>DAI HOC o u 6 c (;f A HA NAI </b>

<b>BAO CAO KfiT QUA THUC HI$N </b>

<b>Dfi TAI DAc BlfiT CA'P DHQG: 2001 - 200.1 </b>

<i><b>T«n dt</b></i>

<b> Ml • </b>

<b>"NGHIEN CtJtJ</b>

<b> T 6 N G HOP, CAU</b>

<b> TRUC VA HOAT TfNH </b>

<i><b>SINH HOC COA CAC HOP CHAT TlTONG TV FLA VON, </b></i>

<b>C6 CHtTA</b>

<b> NHAN DI</b>

<b> VONG" </b>

<i><b>M&s6 : QG.01-02 </b></i>

<i><b>Chu i.hi«m d^ m: GS. TSKH. Nguyin Minh Thdo </b></i>

<b>PHAN MO DAU </b>

MUC LUC

Trang

<i>PHAN Md DAU ' </i>

Danh sdch nhChig ngUiVi tham gia dC tai

<b>3 </b>

<i>Danh muc cac bang s6 li6u ^ </i>

Danh miic c^c hinh ^

TOM TAT NHUNG KET QUA CHINH ^

<i>L Ke't qua v6 mat khoa hoc 4 </i>

2. K6t qua phuc vu thuc te 5

<i>3. K6x qua dao tao 5 </i>

4. K6'l qua niing cao tiOm luc khoa hoc 6

5. Tmh hinh su dung kinh phi 6

ABSTRACT 7

PHAN N O I DUNG CHINH 8

I. DillvAiid^ 8

II. Tdng quan cac vA'n de nghien cuu 9

2.1 Ve pli.ln inij.' (.huven vj I rii*s 9

2.2 Ve cac xeton a. (3-khong no 10

2.3 Vrti net v6 riavon va flavonoit 11

IIL Phuang phap nghien cuu va Ihuc nghiem 12

<i>3.1 Pliuotig phap xac djnh cau tao do tinh khiet yh hoat tfnh sinh hgc ciia 12 </i>

cac hgp cliiit tdng hop dugc

3.2 Tdng hgp cac este ciia phenol va thuc hien phan ung chuyen vi Fries 12

cua chiing

<i>'5-3 HiU(/ng phap chung tdng hgp cac xeton a, \\- khAng no: 14 </i>

3.4 Pliuang phap chung tdng hgp cac hgp chat tuong tu flavon 19

24

<i>4.1 Axetyl hoa c^c phenol vh chuyen vj Fries cua chiing 24 </i>

<i>4.2 Tdng hgp cdc xclon a. \\- khOng no 25 </i>

4.3 Tdng hgp cac hgp chAt tuctng tir flavon co dura nhAn di vong 25

4.4 Tdng hgp cdc hgp chflft kieu pira/olin chi'fa nhrui <li vong 26

4.5 Tinh toan hoa lugng tir 26

4.6 Thdm do hoat tfnh sinh hoc 26

THAM (ilA DE TAI

1. Nguyen Minh Thao - GS. TSKH - Truong Dai hoc Khoa hoc Tu nhicn- DHQG HN.

2. Pham Van Phong - ThS. - Trucmg Dai hgc Khoa hgc Tu nhien- DHQG HN.

3. M6t s6' hgc vien cao hgc va sinh vien.

DANH MUC CAC BANC; SO LI$U

Bang I: Cac san phiim phan ihig chuyen vi Irics

Bang 2: Cdc xeton a. p- khAng no day agienol va iso(rgicnol (E,.;)

Bang 3: Cac xeton a. P- khong no di tir resoxinol (K, s va DKr.. m)

Bang 4: Cac xeton a. P- khong no di ti^ hidroquinon (H,.?)

Bang 5: Cac xeton a, P- khdng-no di ti^ 7- hidroxi- 8- axelylquinolin (Q, 4)

Bang 6: Cac xeton a, p-kh6ng no di lii axit dehidroaxctic ( D H A i n )

Bang 7: Cdc xeton a, P- khdng no di tir 7- hidroxi- 4- metylcumarin (C|.g)

Bang 8: Cdc hgp ch^t tucmg tu flavon di tir agienol va iso(tgicnol

Bang 9: Cdc hgp chat tuong tu flavon di tu resoxinol (F,i,.s va

Bang 10: Cdc hop chat tuong lu flavon di lu hidrcxjuinon (F,,, 0

Bang 11: Cac hgp chat luang tu llavon di lu hidroxiquinolin (F,^,^)

Bang 12: Cac luirp chAI tucmg tu flavon di Iff axit dcliidroaxclic

112)

<i>Bang 13: Cac pira/t)lin chua lutj) phdn (tgicnol v;i isoofgicnol (IVi (d </i>

Bang 14: Cdc pirazolin chira hgp phAn resoxinol (P,(, ^ va F*,,^^, .,):

Bang 15: Cdc pira/olin chua hgp phdn hidrocpiinon (P,,, 0

<i>Bang 16: C{ic piia/olin cliu;i hgp phdn axil deiiidroaxclic</i>

,,)

Bang 17: Cac pinizolin clura vong tiuinolin (P^i i)

Bang 18: Cac pirazolin chua hgp phan cumarin (Pf,.,)

hidroquinon va resoxinol

Bang 20: Kha nang khang khuan va cho'ng nam cua cac xeton a. P- khong no day cumarin

Bang 21: Kha nang khdng khuAii vu chong nam cua cac [)ira/olin day cuiiiarin

DANH MUC CAC HINH

Hinh 1: Phd cong huang ti^ proton cua san phiim chuyen vi Fries 8- axetyl- 7- hidroxi-