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Five Member Heterocyclic Compounds with Nitrogen and Sulfur or Nitrogen, Sulfur and Oxygen (Except Thiazole), Volume 4

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Five Member Heterocyclic Compounds with Nitrogen and Sulfur or Nitrogen, Sulfur and Oxygen (Except Thiazole), Volume 4

L. L. Bambas (Editor)

ISBN: 978-0-470-18803-3 September 2009 416 Pages

Description

The Chemistry of Heterocyclic Compounds, since its inception, has been recognized as a cornerstone of heterocyclic chemistry. Each volume attempts to discuss all aspects – properties, synthesis, reactions, physiological and industrial significance – of a specific ring system. To keep the series up-to-date, supplementary volumes covering the recent literature on each individual ring system have been published. Many ring systems (such as pyridines and oxazoles) are treated in distinct books, each consisting of separate volumes or parts dealing with different individual topics. With all authors are recognized authorities, the Chemistry of Heterocyclic Chemistry is considered worldwide as the indispensable resource for organic, bioorganic, and medicinal chemists.

Preface vii

Part I—Thiadiazoles, Their Derivatives and Selenium Analogs

Derivatives of the 1,2,3-Thiadiazoles and Their Selenium Analogs 3

1.2.3- Thiadiazoles 3

2,2,3-Thiadiazoline-S-dioxides 9

1.2.3- Benzothiadiazoles 10

Discussion 16

Naphthothiadiazoles 31

Benzoselenadiazoles 31

Derivatives of the 1,2,4-Thiadiazoles and Their Selenium Analogs 35

1.2.4- Thiadiazoles 35

I. Derivatives of Perthiocyanic and Isoperthiocyanic Acids 35

Discussion 44

II. 3-and 5-Aryl Substituted 1,2,4-Thiadiazoles 51

III. 1,2,4-Thiadiazolidines (Especially the 3,5-Bis(imino) Derivatives) 54

1.2.4- Selenadiazoles 80

Derivatives of the 1,3,4-Thiadiazoles and Their Selenium Analogs 81

1.3.4- Thiadiazoles 81

2,5- Dialkyl- and the 2,5-Diaryl-1,3,4-thiadiazoles 81

2-1,3,4-Thiadiazolines 89

Glycothiadiazolines or the 2,4-Diphenyl-5-poIyhydroxyalkyl-∆2-1,3,4- thiadiazolines 97

Discussion 102

2- Amino-1,3,4-thiadiazoles and the 5-Imino-∆2-1,3,4-thiadiazolines 103

5-Imino-∆2,-1,3,4-thiadiazolines, 1,3,4-Thiadiazol-5(4)-onesand 1,3,4-Thiadiazol-5(4)-thiones 115

2-Mercapto-∆2-1,3,4-thiadiazolines 120

2,5- Diamino-1,3,4-thiadiazoles and Their Derivatives 124

Discussion of the Chemistry of the 2,5-Diamino-1,3,4-thiadiazoles 132

2-Amino-5-imino-∆2-1,3,4-thiadiazolines and Their Derivatives 141

2-Amino-5-mercapto-1,3,4-thiadiazoles and Related Compounds 143

Discussion 151

2-Amino-∆2-1,3,4-thiadiazol-5(4)-ones 159

Discussion 163

2-Amino-3- and -4-Substituted-1,3,4-thiadiazol-5(4)-ones and Related Compounds 167

Discussion 173

2.5- Dimercapto-1,3,4-thiadiazoIe, 2-Mercapto-1,3,4-thiadiazol-5(4)-thiones and Related Compounds 177

Discussion 185

2-Carboxy-5-thioxo-∆2-1,3,4-thiadiazolines 199

5.6- Dithia-2,3-diazabicyclo [2.1.1]hex-3-enes, 5-Thia-2,3,6-triazabicyclo [2.1.1]-hex-3-enes, and Related ∆2-1,3,4-Thiadiazolines or ψ-1,3,4-Thiadiazoles 200

1,3,4- Selenadiazoles 202

Derivatives of the 2,1,3-Thiadiazoles and Their Selenium Analogs 205

2,1,3- Benzothiadiazoles, 2,1,3-Benzoselenadiazoles, and Related Compounds 205

Discussion 207

4.7- Methanobenzisothiadiazoles 211

Part II—Five-Membered Rings Containing Nitrogen, Sulfur, Selenium, or Oxygen Atoms in Addition to One Sulfur and One Nitrogen

1.2.3- Benzodithiazoles, Benzo-2,3-thiaza-1-thionium Chlorides, and Benzo-1,3-thiaza-2-thionium Chlorides 215

1.3.2- Benzodisulfonazole 217

1.3.4- Dithiazoles 217

1.2.3.4- Dithiadiazoles 218

Condensed Systems Containing 1,2,3,4-Dithiadiazoles 219

1.2.3.4- ThiatriazoIes 219

1.2.3- Oxathiazole-S-oxides or 1,2,3-Oxasulfinazoles 220

1,4,2- Oxathiazoles 221

7-Nitroso-∆3,7-dihydrobenz-2,1,3-oxaselenazoles 222

Part III—Isothiazoles, Their Derivatives and Selenium Analogs

2.1- Benzisothiazoles 225

1.2- Benzisothiazoles, Their Homologs and Selenium Analogs 227

1.2- Benzisothiazoles 227

Discussion 231

3,3'-Bis( 1,2-benzisothiazoline) 238

Naphth[2.3-d]isothiazoles and the Naphth[1.2-d]isothiazoles 238

2.3- Dihydrobenz[d]imidazo[1.2-b]isothiazole 239

Discussion 242

6-Anthr[9.1]isothiazoles and Related Compounds 245

6-Anthr[9.1]isoselenazoles 250

1.2- Benzisothiazolium Compounds 250

1.2- Benzisothiazol-3(2)-ones 253

Discussion 264

1.2- Benzisothiazol-3(2)-thiones 271

1.2- Benzisoselenazol-3(2)-ones 273

1.2- Benzisothiazol-3(2)-one S-oxides 274

1,2- Benzisosulfonazoles, Their Homologs and Derivatives 278

2,3- Dihydro-1,2-benzisosulfonazoles or 2,3-Dihydro-1,2-benzisothiazole-S-dioxides 278

Discussion 287

1,2- Benzisosulfonazoles 297

3- Amino-1,2-benzisosulfonazoles or 3-Imino-2,3-dihydro-1,2-benzisosulfonazoles 302

Saccharin, Benzoic Sulfinide, or 2,3-Dihydro-1,2-benzisosuIfonazol-3-one 318

Discussion 325

2-Substituted Saccharins 327

Thiosaccharin or 2,3-Dihydro-1,2-benzisosulfonazol-3(2)-thione 340

Saccharin Derivatives Substituted in the Benzene Ring or the 2,3-Dihydro-,1,2-Benzisosulfonazol-3(2)-ones and Condensed Systems 342

1,8- Naphthosultams or the 2-, 3-, and 5-Naphth[1.8-cd]isosulfonazoles 354

4- [1.2]Benzisosulfonazolo[4.3-ab]phenazines and the 6-[1.2]Benzisosulfonazolo-[4.3-ab]phenazines 370

10-Camphorsulfonanhydramide and Related Compounds 373

Index 379