Note: Intro -- IMIDAZOLE and Its Derivatives -- Contents -- Preface -- Section 1 CHEMISTRY OF CLASSES AND DERIVATIVES -- I. General Properties and Structure of the Imidazoles -- A. Nomenclature -- B. Physical Properties -- 1. Introduction -- 2. Boiling and Melting Points -- 3. Solubility -- 4. Molecular Weight and Degree of Association -- 5. Viscosity -- 6. Dipole Moments -- 7. Spectroscopic Properties -- (a) Ultraviolet Absorption Spectra -- (b) Raman Spectra -- (c) Chemiluminescence -- 8. Miscellaneous Physical Properties -- C. Chemical Properties -- 1. Basic Strength -- 2. Pseudoacidic Character -- 3. Chemical Stability and Aromatic Character -- D. Structural Considerations -- 1. The Classical Imidazole Formula -- 2. Current Views -- E. Tautomeric Character -- II. The Alkyl- and Arylimidazoles -- A. Synthetic Procedures -- 1. Introduction -- 2. The Radziszewski Synthesis -- 3. The Weidenhagen Synthesis -- 4. Formation from Carbohydrates -- 5. Formation from 2(3H)-Imidazolethiones and Dithiohydantoins -- 6. Formation from Imidazolecarboxylic Acids -- 7. Formation from 2-Imidazolines -- 8. Miscellaneous Procedures -- B. Properties and Chemical Behavior -- 1. General Properties -- 2. Acylation -- 3. Alkylation -- III. The Oxo- and Hydroxyimidazoles and Their Sulfur Analogues -- A. The Oxoimidazoles -- 1. Imidazolecarboxaldehydes -- 2. Imidazole Ketones -- 3. Imidazolones and Thiones -- (a) Nomenclature -- (b) Structural Considerations Regarding the 2(3H)-Imidazolones and Thiones -- (c) 2(3H)-Imidazolones -- (d) 2(3H)-Imidazolethiones -- (e) 2(5H)-Imidazolones -- (f) 4(5H) (or 5(4H))-Imidazolones -- B. The Hydroxyalkylimidazoles -- 1. Monohydroxyalkylimidazoles -- (a) Hydroxymethylimidazoles -- (b) 4(or 5)-(2-Hydroxyethyl)Imidazole -- 2. Polyhydroxyalkylimidazoles -- (a) 4(or 5)-Polyhydroxyalkylimidazoles -- (b)) l-Polyhydroxyalkylimidazoles. , IV. The Halogenoimidazoles -- A. Bromoimidazoles -- 1. Preparative Methods -- 2. Properties -- B. Chloroimidazoles -- C. Chloroalkylimidazoles -- D. Iodoimidazoles -- 1. Preparative Methods -- 2. Properties -- V. The Nitro-, Arylazo-, and Aminoimidazoles -- A. Nitroimidazoles -- 1. Synthetic Methods and Orientation of the Nitro Group -- 2. Properties -- B. Arylazoimidazoles -- 1. Formation and Orientation of the Arylazo Group -- 2. Application of the Diazo Test to the Identification and Estimation of Imidazoles -- 3. Properties -- C. Aminoimidazoles -- 1. 2-Aminoimidazoles -- 2. 4(or 5)-Aminoimidazoles -- D. Histamine -- 1. Discovery, Distribution in Nature, and Pharmacological Effects -- 2. Isolation from Natural Materials -- 3. Quantitative Estimation of Histamine -- (a) Biological Methods -- (b) Colorimetric Methods -- 4. Formation by Microorganisms -- 5. Preparative Methods -- 6. Physical and Chemical Properties -- 7. Structural Analogues of Histamine -- (a) Position Isomers -- (b) Ring-Substitution Products -- (c) N-Monoalkyl- and N-Dialkylhistamine Derivatives -- (d) Histamine Analogues Possessing Longer or Shorter Aliphatic Side Chains -- 8. Pharmacological Specificity -- VI. The Imidazolecarboxylic and Sulfonic Acids -- A. Imidazolecarboxylic Acids -- 1. l-Imidazolecarboxylic Acids -- 2. 2-Imidazolecarboxylic Acids -- 3. 4(or 5)-Imidazolecarboxylic Acids -- 4. 4,5-Imidazoledicarboxylic Acids -- 5. 4(or 5)-Amino-5(or 4)-Imidazolecarboxylic Acids -- (a) Occurrence and Methods of Preparation -- (b) Conversion into Purines -- 6. Histidine -- (a) Discovery, Distribution in Nature, and Structure -- (b) Nomenclature -- (c) Isolation -- (d) Quantitative Estimation -- (e) Synthesis and Resolution -- (f) Physical and Chemical Properties -- (g) Structural Analogues -- B. Imidazolesulfonic Acids -- 1. Structural Considerations. , 2. 1-Imidazolesulfonic Acids -- 3. 2-Imidazolesulfonic Acids -- 4. 4(or 5)-Imidazolesulfonic Acids -- VII. The Imidazolines, 2-Imidazolidones, 2-Imidazolidinethiones, 2-Iminoimidazolidines, and Imidazolidines -- A. Nomenclature -- B. 2-Imidazolines -- 1. Synthetic Methods -- 2. General Properties and Structural Considerations -- 3. Acylation -- 4. Alkylation -- 5. Practical Applications and Pharmacological Action -- C. 2-Imidazolidones -- 1. Synthetic Methods and Properties -- 2. Desthiobiotin and Its Analogues -- D. 2-Imidazolidinethiones -- E. 2-Iminoimidazolidines -- F. Imidazolines -- VIII. The Benzimidazoles -- A. Nomenclature -- B. General Properties -- 1. Boiling Points, Melting Points, and Degree of Association -- 2. Pseudoacidic Character -- 3. Basic Strength and Electronic Structure -- 4. Ultraviolet Absorption Spectra -- 5. Chemical Properties -- 6. Tautomeric Character -- C. Synthetic Procedures -- 1. Introduction -- 2. Formation from Acylated o-Nitroarylamines -- 3. Formation from o-Phenylenediamines and Carboxylic Acids, Acid Anhydrides, Esters, or Amides -- 4. Formation from o-Phenylenediamines and Nitriles -- 5. Formation from o-Phenylenediamines and Imino Ethers or Imino Thioethers -- 6. Formation from o-Phenylenediamines and Aldehydes or Ketones -- 7. Miscellaneous Procedures -- D. The 1-Acylbenzimidazoles and the Bamberger Reaction -- E. The Alkyl- and Arylbenzimidazoles and 1,3-Dialkylbenzimidazolium Salts -- F. The Oxo- and Hydroxybenzimidazoles and Their Sulfur Analogues -- 1. "Oxanhydro Bases" or "Oxbenzimidazoles -- 2. 2(3H)-Benzimidazolones -- 3. 2(3H)-Benzimidazolethiones -- 4. Hydroxyalkylbenzimidazoles -- (a) 1-(PoIyhydroxyalkyl) benzimidazoles (1-Glycosylbenzimidazoles) -- (b) 2-(Monohydroxyalkyl) benzimidazoles -- (c) 2-(Aldopolyhydroxyalkyl) benzimidazoles -- (d) Aldarodibenzimidazoles -- G. The Halogenobenzimidazoles. , 1. Bz-Halogenobenzimidazoles -- 2. 2-Chlorobenzimidazoles -- 3. 2-ChloroalkylbenzimidazoIes -- H. The Nitro- and Aminobenzimidazoles -- 1. Nitrobenzimidazoles -- 2. Aminobenzimidazoles -- (a) Bz-Aminobenzimidazoles -- (b) 2-Aminobenzimidazoles -- (c) Aminoalkyl- and Aminoarylbenzimidazoles -- I. The Benzimidazolecarboxylic and Sulfonic Acids -- 1. Carboxylic Acids -- 2. Sulfonic Acids -- Section 2. SYSTEMATIC SURVEY AND BIBLIOGRAPHY -- Key to Abbreviations -- I. Imidazoles -- A. Alkyl- and Arylimidazoles -- B. Alkyl- and Arylimidazolium Salts -- C. Oxo- and Hydroxyimidazoles and Their Sulfur Analogues -- 1. 2(3H)-Imidazolones -- (a) Alkyl- and Aryl-2(3H)-imidazolones -- (b) Oxo-, Hydroxyalkyl-, and Hydroxyaryl-2(3H)-imidazolones -- (c) Halogenoalkyl-, Aminoalkyl-, and Sulfoalkyl-2(3H)-imidazolones -- (d) 2(3H)-Imidazolonecarboxylic Acids -- (e) Carboxyalkyl- and Carboxyaryl-2(3H)-imidazolones -- (f) Carboxy- and Carboxyalkyl-2(3H)-imidazolones Containing Additional Functional Groups -- 2. 5(4H)-Imidazolones -- 3. 4(5H) (or 5(4H))-Imidazolones -- 4. 2(3H)-Imidazolethiones (2-Mercaptoimidazoles -- (a) Alkyl- and Aryl-2(3H)-imidazolethiones -- (b) 2(3H)-Imidazolethiones Containing Additional Functional Groups -- (c) 2(3H)-ImidazoIethionecarboxylic Acids and Carboxyalkyl- 2(3H)-imidazolethiones -- 5. 4(5H) (or 5(4H))-Imidazolethiones -- 6. Mono- and Polyhydroxyalkyl- and Hydroxyarylimidazoles, Their Ethers and Halogeno Derivatives -- 7. Mercaptoalkyl- and Mercaptoarylimidazoles -- 8. Imidazolecarboxaldehydes and Ketones -- D. Halogenoimidazoles -- 1. Halogeno-, Halogenoalkyl-, and Halogenoarylimidazoles -- 2. Halogenated Alkyl- and Arylimidazolium Salts -- E. Nitroimidazoles -- 1. Nitro- and Nitroarylimidazoles -- 2. Nitroalkyl- and Nitroarylimidazoles Containing Additional Functional Groups -- 3. Nitroalkyl- and Nitroarylimidazolium Salts. , F. Arylazoimidazoles -- G. Aminoimidazoles -- 1. Amino-, Aminoalkyl-, and Aminoarylimidazoles -- 2. Amino-, Aminoalkyl-, and Aminoarylimidazoles Containing Additional Functional Groups -- H. Cyano- and Isocyanatoimidazoles -- I. Imidazolecarboxylic Acids -- 1. Monocarboxylic Acids -- (a) Alkyl- and Arylimidazolecarboxylic Acids -- (b) Imidazolecarboxylic Acids Containing Additional Functional Groups -- (c) Carboxyalkyl- and Carboxyarylimidazoles Including Those Containing Additional Functional Groups -- (1) D-Histidine -- (2) L-Histidine -- (3) DL-Histidine -- (4) Histidine Peptides -- 2. Dicarboxylic Acids -- (a) Alkyl- and Arylimidazoledicarboxylic Acids -- (b) Imidazoledicarboxylic Acids Containing Additional Functional Groups -- (c) Carboxyalkylimidazoleocarboxylic Acids Including Those Containing Additional Functional Groups -- J. Imidazolesulfinic and Sulfonic Acids -- K. Imidazole Arsenicals -- L . Isoimidazoles -- M. Heteroring-Substituted Imidazoles -- 1. Furan Derivatives -- 2. Thiophene Derivatives -- 3. Thiazole Derivatives -- 4. Pyridine Derivatives -- 5. Piperidine Derivatives -- 6. Morpholine Derivatives -- 7. Pyrimidine Derivatives -- 8. Quinoline Derivatives -- 9. Acridine Derivatives -- N. Bi- and Bisimidazoles -- II. Imidazolines -- A. 2-Imilazolines -- 1. Alkyl- and Aryl-2-imidazolines -- 2. Alkyl- and Arylimidazolinium Salts -- 3. Alkyl- and Aryl-2-imidazolines Containing Additional Functional Groups -- 4. 2-Imidazolinecarboxylic and Sulfonic Acids -- B. 3-Imidazolines -- C. 4-Imidazolines -- D. Heteroring-Substituted 2-Imidazolines -- 1. Furan Derivatives -- 2. Thiophene Derivatives -- 3. Triazole Derivatives -- 4. Pyridine Derivatives -- 5. Piperidine Derivative -- 6. Thianaphthene Derivatives -- E. Bi- and Di-2-imidazolines -- III. Imidazolidines -- A. Alkyl- and Arylimidazolidines. , B. Alkyl- and Arylimidazolidines Containing Additional Functional Groups.