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

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