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A Specialist Periodical Report

Organic Compounds of
Sulphur,
Selenium, and Tellurium
Volume 3

A Review of t h e Literature Published between
A p r i l 1972 a n d March 1974
Senior Reporter
D. H. Reid, Department of Chemistry, University of St Andrews
Reporters

G. C. Barrstt, Oxford Polytechnic
R. J. S. Beer, University of Liverpool
D. C. Dittmer, Syracuse University, New York, U.S.A.
1.Durst, University of Ottawa, Ontario, Canada
F. Duus, Odense University, Denmark
J. Fabian, Sektion Chemie der Technischen Universitat, Dresden,
E. Germany
J. G. Gleason, Smith Kline and French Laboratories, Philadelphia,
Pennsylvania, U.S.A.
S. Gronowitz, University of Lund, Sweden
A. W . Johnson, University of North Dakota, U.S.A.
F. Kuner, Royal free Hospital School of Medicine, London

G. Prota, Universita di Napoli, Italy
@ Copyright 1975

The Chemical Society
Burlington House, London W I V OBN


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ISBN: 0 85186 279 9
ISSN: 0305-98 12
Library of Congress Catalog Card No. 77-23818

Filmset in Northern Ireland at The Universities Press, Belfast
Printed by photolithography and bound in Great Britain at
The Pitman Press, Bath.


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Preface
The general aims and structure of this third Volume of ‘Organic Compounds
of Sulphur, Selenium, and Tellurium’ remain those set out in the Preface to
Volume 1.
In accordance with intention expressed in the Preface to Volume 1 to give
more detailed treatment to unusually important or topical subjects, a new
chapter is introduced in this volume entitled ‘f3 -Lactam Antibiotics, Other
Sulphur-containing Natural Products, and Related Compounds’.
‘Theoretical Aspects of Organosulphur and Organoselenium Compounds’
is a review for the period April 1970 to March 1974, with emphasis in this

volume on conjugated systems. A review of the chemistry of Thiepins,
Dithiins, and Thiazepines has been omitted. A review of these subjects,
covering the four-year period April 1972 to March 1976, will appear in
Volume 4. Reviewing of all other material covered in this Volume is for the
two-year period April 1972 to March 1974.

D. H.R.

...

111


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Abbreviations
The following abbreviations have been used:
c.d.
CIDNP
CNDO
cod
DABCO
DCCI
DME
DMF
DMSO
e.s.c.a

e.s.r.
g.1.c.
HMPA
LAH

NBS
n.m.r.
PPP
PY
SCF
THF
t.1.c.
Ts

circular dichroism
chemically induced dynamic nuclear polarization
complete neglect of differential overlap
cyclo-octadiene
diazabicyclo-octane
dicyclohexylcarbodi-imide
dimethoxyethane
NN-dimethylformamide
dimethy1 sulphoxide
electron spectroscopy for chemical analysis
electron spin resonance
gas-liquid chromatography
hexamethylphosphoric triamide
lithium aluminium hydride
N-bromosuccinimide
nuclear magnetic resonance

Pariser-Parr-Pople
pyridine
self-consistent field
tetrahydrofuran
thin-layer chromatography
toluene-p-sulphonyl

V


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Contents
Chapter I

Aliphatic Organo-sulphur
Compounds, Compounds with
Exocyclic Sulphur Functional
Groups, and their Selenium
and Tellurium Analogues
By

G. C.

1

Barrett


1

Textbooks and Reviews

1

2

Spectroscopic and Other Properties
Photoelectron Spectra
Dipole Moments
Nuclear Magnetic Resonance Spectra
Ultraviolet and Circular Dichroism Spectra
Infrared Spectra
Mass Spectra
Electron Spin Resonance Spectra
Other Physical Studies

2

Thiols
Preparations
Thiols as Nucleophiles
Addition Reaction of Thiols
Generation and Reactions of Thiyl Radicals
Reactions of Thiols with Organophosphorus
Compounds
Protection of -SH Groups
Thiols in Biochemistry

Thiolacids and Thiolesters

9

3

4

Sulphides
Preparations
Saturated Aliphatic Sulphides; Aryl Sulphides
Unsaturated Sulphides
Reactions of Sulphides with Carbenes and
Nitrenes; a-Thiocarbenes
Thiocyclopropenium Cations
Sulphides in Synthesis

vii

2
3
4
5
6
7
8
8
9
10
12

14
14
14
15
16
17
17
18
20

24
25
26


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Contents

viii
Sulphides as Reagents
Hete roar y1 Sulphide s
Sulphides Related to Natural Products
Sulphuranes

30
31
31
32


Thloacetals and Related Compounds
Preparations
Reactions

34
34
35

Sulphoxides

37

Preparations
Properties and Reactions of Sulphoxides
a-Sulphinyl Carbanions
&-Halogenated Sulphoxides
p-Keto-sulphoxides and Related Compounds
Unsaturated Sulphoxides
Sulphoxides and Selenoxides in Alkene
Synthesis
Applications of Dimethyl Sulphoxide and
other Sulphoxide s as Oxidants

37
38
40
43
44
45


47
48

Sulphimides and Sulphoximides
Sulphimides
Sulphoximides

50

Sulphones
Preparations
Reduction of Sulphones
Cleavage and Rearrangement of Sulphones
Ring Substitution of Aryl Sulphones
a-Halogenosulphones
Other a-Functional Sulphones
P-Keto-sulphones
a-Sulphonyl Carbanions
Bis(sulphony1)methanes
Unsaturated Sulphones
Sulphones in Synthesis

52

Sulphenic Acids
Preparations
Reactions of Sulphenic Acids
Sulphenates
Sulphenyl Halides
Subhenamides


58
58
59
59
60
62

50
51

52
53
53
54
54
54
55
55
55
56

57


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ix

Contents
10


Thiocyanates and Isothiocyanates

Preparations of Thiocyanates
Properties of Thiocyanates
Preparations of Isothiocyanates
Reactions of Isothiocyanates

64
64
65
65
66

11

Sulphinic Acids
Preparations
Reactions of Sulphinic Acids
Sulphinate Esters
Sulphinyl Halides
Sulphinamides

67
67
68
69
69
70


12

Sulphonic Acids
Preparation
Sulphonates
Sulphonyl Peroxides
Sulphonyl Halides and Sulphenes
Sulphonamide s
Sulphonyl Cyanides and Isocyanates
Sulphonyl Azides

70
70

13

Disulphides, Polysulphides, and their
Oxy-sulphur Analogues

Preparations of Disulphides, Hydropolysulphides, and Polysulphides
Reactions of Disulphides
Thiosulp hinate s
Thiolsulphonates
a-Disulphones

Chapter 2

Small Ring Compounds of Sulphur
and Selenium
B y D.


12

74
74
75
77
77
78
78
80
82
83
84

85

C. Dittrner

1

Reviews

85

2

Thiirans
Physical Properties and Theoretical
Treatments

Formation
Intermediates in Reactions
Chemical Properties

85
85

86
92
95


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Contents

X

Thiiranium Cations

Formation
Intermediates in Reactions
Thiiran 1-Oxides

Formation
Intermediates in Reactions
Chemical and Physical Properties
5

Thiiran 1,l-Dioxides


Physical Properties and Theoretical
Considerations
Formation
Intermediates in Reactions
6

Thiiren Derivatives

Theoretical Considerations
Intermediates in Reactions
Chemical Properties
7

8

Three-membered Rings containing Sulphur
and One or Two other Heteroatoms
Formation and Properties
Intermediates in Reactions
Thietans

Physical Properties
Formation
Intermediates in Reactions
Chemical Properties

98
98
98
103

103
105
106
107
107
108
108

110
110
110
111
112
112
113

114
114
115
118
119

Thietan 1-Oxides

121

Thietan 1,l-Dioxides
Physical Properties
Formation and Chemical Properties


121

11

Thiets

123

12

Thiet 1,l-Dioxides and Thiet 1-Oxides

125

13

Four-membered Rings containing Nitrogen and
One Sulphur Atom

126

9

10

Thiazetidines and Thiazetes
Oxathiazetidines
Rings containing Two Nitrogen Atoms

121

121

126
129
129


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Contents

xi
14

Four-membered Rings containing Oxygen and
One Sulphur Atom

Sultones and Sultines (1,2-Oxathietan
2,2-Dioxides and 1,2-0xathietan 1-Oxides)
Oxathietans, Oxathiets, and Dioxathietans

130
130
131

15

1,2-Dithietans and 1,3-Dithietans

131


16

1,ZDithiets

135

17

Selenium Derivatives

137

Chapter 3

Saturated Cyclic Compounds of
Sulphur and Selenium

139

B y T. Durst

1

Introduction

2

Thiolans, Thians, Thiepans, Thiocans, and
their Oxides and Dioxides


Synthesis
Reactions and Properties
3

Compounds with Two Sulphur or Selenium Atoms
in the Ring and their Oxy-sulphur Analogues

Cyclic Disulphides
1,3-Dithiolans and 1,3-Dithians
Synthesis
React ions
1,4-Dithians, 1,4-Dithiepans, and
1,5-Dithiocans
4

Compounds containing Three or More
Sulphur Atoms

1,2,4-Trithiolans, 1,3,5-Trithians, and
1,2,4,5Tetrathians
Large Ring Disulphides, including
Sulphur-containing Cyclophanes
5

Compounds containing Sulphur or
Selenium and Oxygen

Sultines, Sultones, and Related Systems
1,3-Oxathiolans, 1,3-0xathians,
1,4-Oxathians, and Related Compounds

Cyclic Sulphites and Related Compounds

139
139
139
145
157
157
161
161
164
172

174
174
176

179
179
183
186


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xii

Contents

Chapter 4


P-Lactam Antibiotics, other
Su I p hu r-contai ni ng Natural
Products, and Related
Compounds

190

B y J. G. Gleason

1

Introduction

190

2

Fermentation and Biosynthetic Aspects

191

3

Modification of the @-LactamRing System
Modification at C-6(7)
Epimerization
Modifications in the Thiazine Ring

194

194
198
199

4

Partial Synthesis of Cephalosporins
and Penicillins

202

Total Synthesis of Penicillins and
Cephalosporins

209

6

Structure-Activity Considerations

213

7

Epidithiodioxopiperazines

215

8


Other Sulphur-containing Natural Products

217

5

Chapter 5

Thiocarbonyl and Selenocarbonyl
Compounds

219

B y F. Duus

1

Introductiod
Reviews

219
219

2

Thioaldehydes

220
220
22 1

222

Synthesis
Transient Species
Reactions
3

Thioketones and Selenoketones
Synthesis
Transient Species
Metal Complexes
Reactions

222
222
229
23 1
233

4

Thioketens and Selenoketens

24

5

Thiocarbonyl Ylides, Thiocarbonyl SImides,
and their Selenium Analogues


246


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Contents

Xlll

6

Sulphines

248

7

Sulphenes

252

8

Thioamides and Selenoamides
Synthesis
Metal Complexes
Reactions


254
254
26 1
262

9

Thioureas and Selenoureas
Synthesis
Reactions

267
267
273

10

Thiosemicarbazides and Selenosemicarbazides
Synthesis
Reactions

279
279
28 1

11

Thionocarboxylic and Dithiocarboxylic Acids,
their Derivatives, and the Selenium Analogues
Synthesis

Reactions

284
284
289

Thionocarbonates, Thionodithiocarbonates,
Trithiocarbonates, and their Selenium Analogues
Synthesis
Reactions

295
295
2%

Thionocarbamic and Dithiocarbamic Acids,
their Derivatives, and their Selenium Analogues
Synthesis
Reactions

300
300
303

12

13

14


Physical Properties
Structure
Tautomerism
Hydrogen Bonding
Polarization Effects, Restricted Rotation,
and Isomerization Phenomena
Crystal and Molecular Structures
Spectra
Ultraviolet Spectra
Infrared and Raman Spectra
Rotational Spectra
N.M.R. Spectra
E.S.R. Spectra
Photoelectron and ESCA Spectra
Mass Spectra

309
309
309
31 1

311
3 14
315
315
316
318
318
3 19
3 19

319


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xiv
Other Physical Properties
Electrochemistry
Dipole Moments
Acidity and Basicity Measurements

Chapter 6

Ylides of Sulphur, Selenium, and
Tellurium, and Related
Structures

Contents
320
320
32 1
321

322

B y A. William Johnson

1

Introduction


322

2

Sulphonium Ylides

322
322
328
330
335

Methods of Synthesis
Physical Properties
Chemical Stability
Reactions of Sulphonium Ylides
3

Oxysulphonium Ylides
Synthesis and Properties
Reactions of Oxysulphonium Ylides

346
346
347

4

Sulphinyl Ylides


352

5

Sulphonyl Ylides

355

6

Sulphenes

356

7

Sulphines

359

8

Sulphur Imines
Iminosulphuranes
Sulphurdi-imines
Sulphonedi-imines
Imino-oxysulphuranes

363
363

369
37 1
373

9

Sulphonyl- and Sulphinyl-amines

38 1

10

Ylides of Selenium and Tellurium

385

Chapter 7

Heterocyclic Compounds of
Qu ad ricova lent Su Ip h u r

387

B y D. H. Reid

1

Introduction

387


2

Thiabenzenes

387

3

Azathiabenzenes

39 1


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xv

Contents
4

Thieno[3,4-c]thiophens and Related Compounds
Thieno[ 3,4-c]thiophens
Thieno[ 3,4- c]f uran s
Thieno[3,4-~]pyrroles
Thieno[3,4-c]pyrazoles

392
392
3%
3%

398

5

Miscellaneous Ring Systems

398

Chapter 8

Thiophens and their Selenium and
Tel lu ri u m Analogues
By

400

S. Gronowitz

1

General

400

2

Monocyclic Thiophens

400


Synthesis of Thiophens by Ring-closure
Reactions
Syntheses of Thiophens from other
Ring Systems
Electronic Spectra
1.r. Spectra
Dipole Moments
N.M.R. Spectra
Various Physical Properties
Electrophilic Substitution
Electrophilic Ring-closure
Radical Reactions
Nucleophilic Substitutions
Metallation and Halogen-Metal Exchange
Photochemistry of Thiophens
Electrochemical Reactions
The Structure and Reactions of Hydroxyand Mercapto-thiophens
Aminothiophens and their Reactions
Side-chain Reactivities
Chloromethyl Derivatives
Reactions of Thiophen Aldehydes and
Ketones
Various Side-chain Reactions
Bi- and Poly-heterocycles
Thiophen Analogues of Porphyrins
Reactions Leading to Destruction of the
Thiophen Ring
Naturally occurring Thiophens
Thiophens of Pharmacological Interest


400
408
409
410
41 1
412
412
413
416
417
419
42 1
424
425
425
427
430
43 1
432
435
438
439
440
442
443


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xvi


Contents
3

Thienothiophens, their Benzo-derivatives,
and Analogous Compounds

Synthesis
Theoretical Studies and Physical Properties
Substitution Reactions
Non-classical Thienothiophens
4

5

Benzothiophens and their Benzo-fused Systems
Synthesis of Benzothiophens by
Ring-closure Reactions
Physical Properties
Electrophilic Substitution
Nucleophilic Substitution, Metallation,
and Halogen-Metal Exchange
Side-chain Reactions
Photochemistry
2- and 3-Hydroxybenzo[b]thiophen Systems
Reaction at Sulphur
Pharmacologically Active Compounds
Thiophen Analogues of Polycyclic
Aromatic Hydrocarbons

Thiophen Analogues of Anthracene

and Phenanthrene
Thiophen Analogues of Helicenes
Thiophen Analogues of Indene and Fluorene
Thiophen-f used Tropylium Ions and
Related Compounds
6

Thiophens Fused to Five-membered Aromatic
Heterocyclic Rings

Pyrrole- and Furan-fused Thiophens and
Related Compounds
Pyrazole-, Thiazole-, and Imidazole-f u sed
Thiophens
7

Thiophens Fused to Six-membered Aromatic
Heterocyclic Rings
Thiophen Analogues of Quinoline
Thiophen Analogues of Isoquinoline
Pyrimidine-fused Systems
Pyridazine-fused Systems
Thiophens Fused with other Nitrogencontaining Heterocycles
Miscellaneous Fused Systems

447
447
447
447
448

449

449
453
454
455
456
457
458
458
459
461

46 1
462
462
465
467
467
47 1
473
473
474
476
478
480
480


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xvii

Contents
8

Selenophens and Tellurophens

General
Monocyclic Selenophens
Ring-closures
Physical Properties
Electrophilic Substitution
Nucleophilic Substitution, Metallation,
and Halogen-Metal Exchange
Side-chain Reactivities
Benzo[ b]selenophens and their Benzo-fused
Derivatives
Selenophens Fused to Five-membered Rings
Selenophens Fused to Six-membered
Heterocyclic Aromatic Rings
Tellurophens

Chapter 9

6a-Th iat h iop ht he ns a nd Re Iat ed
Compounds

48 1
48 1
482

482
482
483
483
484
485
487
49 I
49 1

494

B y R. J. S. Beer

Chapter 10

Introduction

494

Structural and Theoretical Studies

494

Synthesis of 6a-Thiathiophthens

4%

Properties and Reactions of
6a-Thiathiophthens


498

I ,2-Dithiolylidene Aldehydes and Ketones

499

Multisulphur Systems

50 1

6a-Selenathiophthens

503

Other Analogues of 6s-Thiathiophthen

503

1,2- a n d 1,3-Dithioles
R. J. S. Beer

509

By

1

1,2-Dithioles and Related Compounds


509

2

1,2-Dithiolium Salts

512

3

1,3-Dithioles and Related Compounds

517

4

1,3-Dithiolium Salts

519

5

1,3-Dithiole Carbene Reactions and
Bi-1,3-dithioles

520


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Contents


x viii

Chapter 11

Thiopyrans and Related
Compounds

523

By R . J. S. Beer

3

2H-Thiopyrans and Related Compounds

523
523
526

4

4H-Thiopyran Derivatives

527

5

Thiopyran 1,l-Dioxides


528

6

Thiopyrylium Salts

530

7

Thiochromans and Thiochromenes

8

Thiochromones and Thiocoumarins

9

Thioisochromans and Related Compounds

531
534
535

1

Introduction

2


Dihydrothiopyrans

10
11

C'hapter 12

Thioxanthenes, Thioxanthones, and
Related Compounds
Complex Thiopyran Derivatives

lsot h iaz oles

537
539

541

B y F. Kurzer

1

Introduction

541

2

Synthesis


541
542
542
543
543
544
544
545
545
545

From Oxathiazolones
From Meso-ionic 1,3,2-0xathiazolium-5-olates
From Isoxazoles
From 1,ZDithiolans
Condensation of Nitriles and Dialkyl Sulphites
Photoisomerization of Thiazoles
From Thione-S-imides
From p-Aminocrotonic Esters
Type F Syntheses
3

Physical Properties

546

4

Chemical Properties
Free-radical Reactions

Alkylation and Quaternization
Nitration
Nucleophilic Reactions
Further Rearrangements

547
547
547
548
548
55 1


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xix

Contents
Complex Formation
Biochemical
5

1,2-Benzisothiazoles

1,2-Benzisothiazole 1,l-Dioxides

553
553
554


555

6

2,l-Benzisothiazoles

557

7

Naphthisothiazoles and Isothiazolanthrene

560

8

Other Condensed Ring Systems
incorporating Isothiazole

Thieno[2,3-~]isothiazoles
Isothiazolopyridines
Isothiazolo[4,3-d] thioisocoumarin
9

Isoselenazoles

56 1
56 1
562
563

564

Chapter 13 Thiazoles and Related Compounds 566
B y F. Kurzer

1

Introduction

566

2

Synthesis of Thiazoles
Hantzsch’s Synthesis
Other Type A Syntheses
Type B Syntheses
Type F Syntheses
Type H Syntheses
Type J Syntheses
Syntheses from the Pre-formed Thiazole Ring

567
567
567
568
569
570
57 1
57 1


3

Physical Properties of Thiazoles

572

4

Chemical Properties of Thiazoles

573
573
573
574
575
577
577
578
578
579
579
580
580
580

Photolytic and Related Reactions
Quaternization and Alkylation
Acylation
Electrophilic Substitution

Nucleophilic Substitution
Ring Expansion to 1,4-Thiazines
Dimerization
Ylides of Thiazolium Ions
Deh y drothiazole
Miscellaneous Reactions
Cyanine Dyes
Analytical
Meso-ionic Thiazoles


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xx

Contents
58 1

5

Biochemical Aspects of Thiazoles

6

Synthesis of A2-Thiazolines
Type A Syntheses
Type B Syntheses
Type D Syntheses
Type E Syntheses
Type F Syntheses
Type H Syntheses

Ring Expansion of Aziridines
Type K Syntheses
Type N Syntheses

582
582
582
582
583
583
584
584
585
585

7

Physical Properties of A’-Thiazolines

8

Chemical Properties of A2-Thiazolines

586
587

9

Synthesis of A4-Thiazolines


592

10

Properties of A4-Thiazolines

595

11

Synthesis of Thiazolidines
Type A Syntheses
Type B Syntheses
Type D Syntheses
Type E Syntheses
Type G Syntheses

5%
5%
600
601
602
605

12

Properties of Thiazolidines

606
606

606
607
608
608
609
610.
61 1
61 1

Spectra
N-Alk ylation
Ring Scission
Condensations at the 5-Methylene Group
Grignard Reagents
Penicillins
Pep tides
Biochemical and Physiological Properties
Rhodanine, Isorhodanine, and Thiorhodanine
13

Chapter 14

1

2

Selenazoles

Condensed Ring Systems
Incorporating Thiazole

By F. Kurzer
Introduction

Synthesis of Benzothiazole
From o-Aminothiophenols
Jacobson-Hugershoff Synthesis

615

617
617
617
617
619


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Other Type B Syntheses
Type C Syntheses

xxi
62 1
621

3

Physical Properties of Benzothiazoles

624


4

Chemical Properties of Benzothiazoles
Homolysis, Oxidation, and Reduction
Nucleophilic Substitution
Nitration
Organometallic Reagents
Condensations
Rearrangement
Ring Expansion to 1,4-Thiazines
Polymethine and other Dyes
Metal Complexes
Chemiluminescence and Bioluminescence
Biochemical and Miscellaneous

626
626
627
629
629
631
634
635
636
638
638
641

5


Structures comprising Two Five-membered
Rings
Thiazolo[3,2-d]tetrazoles
ThiazoIo-[2,3-c]- and -[3,2-b]-syrn-triazoles
Imidazo[2,l-b]thiazoles
PyrroloC2,1-b]thiazoles
Thieno[2,3-d]thiazoles
Structures comprising One Five-membered
and One Six-membered Ring
Thiazolo[2,3-b][ 1,3,5]thiadiazines

6

Thiazolo[3,2-a]-syrn-triazines
Meso-ionic Thiazolo[3,2,-a]-syrntriazine-5,7-diones
Thiazolo[2,3-c][1,2,4]triazines
Thiazolo[4,5-d]pyridazines
Thiazolo[3,2-a]pyrimidines
Meso-ionic Thiazolo[3,2-a]pyrimidine5,7-diones
Thiazolo[3,2-c]pyrimidines
Thiazolo[4,5-d]pyrimidines
Thiazolo[5,4-d]pyrimidines
Thiazolo[3,2-a]pyridines
Thiazolo[4,5-b]pyridines
Thiazolo[5,4-blpyridines
7

Structures comprising Two Five-membered
and One Six-membered Ring

s yrn-Triazolo[3,4-b]benzothiazoles
Thiazolo[3,2-e]purines

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xxii


Contents
Thiazolo[2,3-flpurines
Imidazo[2,1-b]thiazolo [5,4-blpyridines
Thiazolo[ 3,2-a]benzimidazoles

Thiazolo[4,5-flindazoles
Imidazo[2,l-b]benzothiazoles
Pyrrolo[ 1,2-a]thiazol0[5,4-e]pyrimidines
Indolino[2,l-b] thiazoles
8

Structures comprising One Five-membered
and Two Six-membered Rings

Pyrido[3,2-d]thiazolo[ 3,2-a]pyrimidines
Pyrimido[2,3-b]thiazolo[5,4-b]pyridines
Pyrimido[2,l-b]benzothiazoles
Thiazolo[4,5-c]cinnolines
Thiazolo [2,3-b]quinazolines

Thiazolo[4,5-b]quinoxalines
Thiazolo[3 ,2-a]-quinolines
(and -isoquinolines)
Thiazolo[4,5-fl- and - [5,4-fl-quinolines
Thiazolo[2,3-a]isoquinoline
Thiazolo-[4,5-h]-, -[5,4-fl-, and
-[5,4- h]-isoquinolines
9


10

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Structures comprising Two Five-membered
and Two Six-membered Rings

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Pyrido[2,3-d]imidazo[2,l-b]thiazolo[5,4-b]pyridine and Related Systems

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Structures comprising One Five-membered
and Three Six-membered Rings

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Thiazolo[4,5-b]phenothiazine
Pyrido[ 3,2-a]thiazolo [2,3- b]quinazolines

Benzothiazolo- [2,3-b]- and
-[3,2-a]-quinazoline s

C’hapter 15

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Thiadiazoles and Selenadiazoles

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By F. Kurzer
1

Introduction

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2


Synthesis of 1,2,3-ThiadiazoIes
Pechmann’s Synthesis
From Hydrazones
By Other Reactions

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3

Properties of 1,2,3-Thiadiazoles

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Contents

xxiii
Synthesis and Properties of
1,2,3-Selenadiazoles

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5

Synthesis of 1,2,3-Benzothiadiazoles


675

6

Properties of 1,2,3-Benzothiadiazoles

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7

Synthesis of [1,2,3]Thiadiazolo[5,4-b]pyridine

679

8

Synthesis of 1,2,4-Thiadiazoles

Syntheses
Syntheses
Syntheses
Syntheses

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Properties of 1,2,4-Thiadiazoles


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Condensed Systems incorporating
1,2,4-Thiadiazoles

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11

Synthesis of 1,3,4-Thiadiazoles

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12

Properties of 1,3,4-Thiadiazoles
A2-1,3,4-Thiadiazolines
A3-1,3,4-Thiadiazolines
Meso-ionic 1,3,4-Thiadiazoles

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13

Synthesis and Properties of
1,3,4-Selenadiazoles


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14

Condensed 1,3,4-Thiadiazoles

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15

Synthesis of 1,2,5-Thiadiazoles

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16

Properties of 1,2,5-Thiadiazoles

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Properties of 2,1,3-Benzothiadiazoles

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18

Synthesis and Properties of


4

Type
Type
Type
Type
9
10

19

B
C
D
E

2,1,3-Benzoselenadiazoles

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Condensed 1,2,5-Thiadiazoles

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C’hapter 16 Thiazines

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By G. Prota


1

Introduction

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2

1,2-Thiazines

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Simple 1,2-Thiazines
Benzo-1,Zthiazines