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.

Richard H. Wiley is the editor of Pyrazolones, Pyrazolidones, and Derivatives, Volume 20, published by Wiley.

Paul F. Wiley is the editor of Pyrazolones, Pyrazolidones, and Derivatives, Volume 20, published by Wiley.

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