Imidazole and Its Derivatives, Part 1, Volume 6

Preface ix

Section I Chemistry of Classes and Derivatives

I. General Properties and Structure of the Imidazoles 3

A. Nomenclature 3

B. Physical Properties 5

C. Chemical Properties 13

D. Structural Considerations 17

E. Tautomeric Character 26

II. The Alkyl- and Arylimidazoles 33

A. Synthetic Procedures 33

B. Properties and Chemical Behavior 45

III. The Oxo- and Hydroxyimidazoles and Their Sulfur Analogues 55

A. The Oxoimidazoles 55

B. The Hydroxyalkylimidazoles 99

IV. The Halogenoimidazoles 111

A. Bromoimidazoles 111

B. Chloroimidazoles 119

C. Chloroalky limidazoles 121

V. The Nitro-, Arylazo-, and Aminoimidazoles 127

A. Nitroimidazoles 127

B. Arylazoimidazolcs 136

C. Aminoimidazoles 141

D. Histamine 143

VI. The Imidazolecarboxylic and Sulfonic Acids 175

A. Imidazolecarhoxylic Acids 175

B. Imidazolesulfonic Acids 206

VII. The Imidazolines, 2-Imidazolidones, 2-Imidazolidinethiones, 2-Iminoimidazolidines, and Imidazolidines 213

A. Nomenclature 213

B. 2-ImidazoIines 213

C. 2-Imidazolidones 226

D. 2-Imidazolidinethiones 234

E. 2-Iminoimidazolidines 238

F. Imidazolidines 242

VIII. The Benzimidazoles 247

A Nomenclature 247

B General Properties 248

C. Synthetic Procedures 258

D. The 1-Acylbenzimidazoles and tire Bamberger Reaction 273

E. The Alkyl- and Arylbenzimidazoles and 1,3-Dialkyibenzimiduzolium Salts 276

F. The Oxo- and Hydroxybenzimidazolcs and Their Sulfur Analogues 284

G The Halogenobenzimidazoles 300

H The Nitro- and Aminobenzimidazoles 304

I. The Benzimidazolecarboxylic and Sulfonic Acids 313

Section 2 Systematic Survey and Bibliography

Key to Abbreviations 320

I. Imidazoles 327

A. Alkyl-and Arylimidazoles 327

B Alkyl- and Arylimidazolium Salts 330

C. Oxo- and Hydroxyimidazolos and Their Sulfur Analogues 330

D. Halogenoimidazoles 342

E. Nitroimidazoles 345

F. Arylazoimidazoles 346

G. Aminoimidazoles 347

H. Cyano- and Isocyanatoimidazolcs 351

I. Tinidazolcearboxylic Acids 352

J. Imidnzolcsulftnic and Sulfonic Acids 363

K. Imidazole Arscnicals 363

L. Isoimidazolcs 363

M. Heteroring-Substituted Imidazoles 364

N Bi- and Bisimidazoles 366

II. Imidazolines 367

A. 2-Tmidazolines 367

B. 3-Imidazolines 372

C. 4-Imidazolines 372

D. Heteroring-Substituted 2-Imiriaznliiics 372

III. Imidazolidines 373

A. Alkyl- and Arylimidazolidines 373

B. 4- and 5-Imidazolidones 378

C. 2-Iraidazolidinethiones (Ethylenethioureas) 378

D. 4-Imidazolidinethiones 379

E. 2-Iminoimiriazoliriines (Ethyleneguanidines) 379

V. Benzimidazoles 379

A. Alkyl- and Arylbenrimidazoles 379

B. Alkyl- and Arylbenzimidazolium Salts 382

C. Oxo-and Hydroxybenzimidazoles and Their Sulfur Analogues 382

D. Halogeno-, Halogenoalkyl-, and Halogenoarylbenzimidazoles 388

E. Nitro-, Nitroalkyl-, and Nitroarylbenzimidazoles Including Those Containing Additional Functional Groups 388

F. Aminobenzimidazoles 389

G. Cyanobenzimidazoles 394

H Benzimidazolecarboxylic Acids 395

I. Benzimidazolcsulfonic Acids, Sulfoalkyl-, and Sulfoarylbenzimidazoles 398

J. Benzimidazole Arscnicals 398

K. 2,3-DihydroIxaizimidazoles (Benzimidizolines) 399

L. Heteroring-Substituted Benzimidazoles 399

M Bi-, Di-, and Bisbonzimidazoles 401

Bibliography 401

Subject Index 421