Pyrazolones, Pyrazolidones, and Derivatives, Volume 20

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.

Part 1. Chemistry Chapter I. General 1. Introduction 3 2. Historical 4 3. Structure 5 4. Synthesis 9 5. Physical Properties 10 6. Chemical Properties 11 Chapter II. Pyrazolin-5-ones 1. Introduction 13 2. Unsubstituted Alkyl, Alicyclic, Aralkyl, Aryl and Heterocyclic Substituted Derivatives 13 A. 2-Pyrazolin-5-ones 13 (1) Syntheses 13 (2) Physical Properties 18 (3) Chemical Properties 19 (4) Hydroxyalkyl Types 29 (5) Aminoalkyl Types 30 (6) Bis(2-pyrazolin-5-ones) 31 B. 2-Pyrazolin-5-thiones 40 C. 5-Imino-2-pyrazolines 41 D. 3-Pyrazolin-5-ones 46 (1) Syntheses 46 (2) Properties 49 (3) Bis(3-pyrazoIin-5-ones) 56 E. 3-Pyrazolin-5-thiones and -5-selenones 58 F. 5-Imino-3-pyrazolines 59 3. Hydroxy and Mercapto Derivatives 61 A. 2-Pyrazolin-5-ones 61 B. 3-Pyrazolin-5-ones 63 4. Amino, Imino, Hydrazino, Azo and Related Derivatives 65 A. 2-Pyrazolin-5-ones 65 B. 3-Pyrazolin-5-ones 76 5. Halogen Substituted Derivatives 81 A. 2-Pyrazolin-5-ones 81 B. 3-Pyrazolin-5-ones 83 6. Nitroso Substituted Derivatives 85 A. 2-Pyrazolin-5-ones 85 B. 3-Pyrazolin-5-ones 87 7. Nitro Substituted Derivatives 88 A. 2-Pyrazolin-5-ones 88 B. 3-Pyrazolin-5-ones 89 8. Aldehydes and Ketones 89 A. 2-Pyrazolin-5-ones 89 B. 3-Pyrazolin-5-ones 92 9. Carboxylic Acids and Derivatives 95 A. 2-Pyrazolin-5-ones 95 B. 3-Pyrazolin-5-ones 100 10. Sulfonic Acids and Derivatives 101 A. 2-Pyrazolin-5-ones 101 B. 3-Pyrazolin-5-ones 102 11. Functional Group Substituents on Nitrogen 102 A. 2-Pyrazolin-5-ones 102 B. 3-Pyrazolin-5-ones 10+ 12. Mercury Substituted Derivatives 104 A. 2-Pyrazolin-5-ones 104 B. 3-Pyrazolin-5-ones 105 13. Metallic and Non-metallic Complexes 105 A. 2-Pyrazolin-5-ones 105 B. 3-Pyrazolin-5-ones 107 14. Miscellaneous Derivatives 108 Chapter III. 2-Pyrazolin-4-ones Ill Chapter IV. 2-Pyrazolin-4,5-diones 114 Chapter V. 3-Pyrazolidinones 115 Chapter VI. 3,4-Pyrazolidinediones 120 Chapter VII. 3,5-Pyrazolidinediones 1. Introduction 123 2. Alkyl, Aralkyl, Heterocyclicalkyl and Aryl Substituted Derivatives 124 3. Hydroxy and Alkoxy Substituted Derivatives 128 4. Amino and Azo Substituted Derivatives 128 5. Halogen Substituted Derivatives 129 6. Nitroso Substituted Derivatives 129 7. C-Acyl Substituted Derivatives 129 8. N-Acyl Substituted Derivatives 130 Chapter Vlll. 5-Imino-3-pyrazolidinones 1. Introduction 131 2. Alkyl, Alicyclic, Aralkyl, Heterocyclicalkyl, Heterocyclic and Aryl Substituted Derivatives 132 3. Functional Group Derivatives 137 Chapter IX. Miscellaneous 3,5-Pyrazolidinediones and Analogs 139 Part 2. Applications Chapter I. Medical 143 Chapter II. Color Photography 148 Chapter III. Textile and Fabric Dyes 152 Chapter IV. Analytical Reagents 155 Chapter V. Miscellaneous 157 Appendix. Systematic Tables of Pyrazolones and their Derivatives 161 References 483 Index 525