The 1,2,3- and 1,2,4-Triazines, Tetrazines and Pentazines, Volume 10

by Erickson, John G.; Wiley, Paul F.; Wystrach, V. P.

• ISBN13: 9780470182734
• ISBN10: 0470182733
• Edition: 1st
• Format: Hardcover
• Copyright: 2007-04-13
• Publisher: Wiley-Interscience

Summary

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.

Author Biography

John G. Erickson and Paul F. Wiley are the authors of The 1,2,3- and 1,2,4-Triazines, Tetrazines and Pentazines, Volume 10, published by Wiley.

Table of Contents

I. The 1,2,3-Triazrnes 1
By John G. Erickson

Introduction 1

1. Uncondensed 1,2,3-Triazines 3

A. Unbridged 1,2,3-Triazine Rings 3

B. 1,2,3-Triazine Rings with Valence Bridges 4

2. 1,2,3-Triazine Rings Condensed with Carbocycles 5

A. Condensed with Benzene 5

(1) 1,2,3-Benzotriazine 5

(2) 1,2,3-Benzotriazines with Valence Bridges 27

B. Condensed with Naphthalene 31

(1) Condensed with the 2,3 Positions of Naphthalene 31

(2) Condensed with the 1,8 Positions of Naphthalene 31

3. 1,2,3-Triazine Rings Condensed with Heterocycles 34

A. Condensed through Two Carbon Atoms 34

(1) Condensed with the Thiazole Ring 34

(2) Condensed with the Pyrazole Ring 35

B. Condensed through a Carbon Atom and a Nitrogen Atom 36

(1) Condensed with the Pyrazole Ring 36

(2) Condensed with the Thiazole Ring 37

(3) Condensed with the Imidazole Ring 38

(4) Condensed with the Pyrimidine Ring 41

Bibliography 41

II. The 1,2,4-Triazines 44
By John G. Erickson

Introduction 44

1. Uncondensed 1,2,4-Triazines 45

A. Unbridged 1,2,4-Triazine Rings 45

B. 1,2,4-Triazine Rings with Valence Bridges 85

2. 1,2,4-Triazine Rings Condensed with Carbocycles 88

A. As Parts of Spiro Ring Systems 88

B. Condensed with Alicyclic Ring Systems in 1,2 Positions 89

(1) Condensed with Cyclopentane 89

(2) Condensed with the Norcamphane System 89

(3) Condensed with the Cyclopentaphenanthrene Ring System 91

(4) Condensed with the Spiro [4,5] decane Ring System 92

(5) Condensed with the Phenanthridine Ring System 92

C. Condensed with the Benzene Ring 93

(1) 1,2,4-Benzotriazine 93

(2) Two 1,2,4-Triazine Rings Condensed with One Benzene Ring 111

D. Condensed with Naphthalene 112

(1) Condensed with the 2,3 Positions of Naphthalene  112

(2) Condensed with the 1,2 Positions of Naphthalene 113

E. Condensed with Higher Aromatic Ring Systems 120

(1) Condensed with the Acenaphthene System 120

(2) Condensed with the Phenanthrene System 121

3. 1,2,4-Triazine Rings Condensed with Heterocycles 124

A. Condensed through Carbon Atoms 124

(1) Condensed with the Pyran Ring 124

(2) Condensed with the Indole Ring System 125

B. Condensed through a Carbon Atom and a Nitrogen Atom 128

(1) Condensed with the Pyrazole Ring 128

(2) Condensed with the Indazole Ring System 131

(3) Condensed with the 1,2,4-Triazole Ring 132

Bibliography 132

III. The 1,2,3,4-Tetrazines 138
By V.P.Wystrach

Introduction 138

1. Uncondensed 1,2,3,4-Tetrazines 140

A. 1,2,3,4-Tetrazine 140

B. Dihydro-1,2,3,4-Tetrazines 141

(1) Substituted in the 2- and 3-Positions with Aryl Groups 142

(2) Substituted in the 2- and 3-Positions with Benzoyl Groups 150

(3) 1,2- and 2,5-Dihydro-1,2,3,4-Tetrazines 159

C. Tetrahydro-1,2,3,4-Tetrazines 162

D. Hexahydro-1,2,3,4-Tetrazines 163

E. 1,2,3,4-Tetrazines with Valence Bridges 164

2. 1,2,3,4-Tetrazine Rings Condensed with Carbocycles 165

A. Condensed with a Benzene Ring 165

B. Condensed with a Naphthalene Ring 168

3. 1,2,3,4-Tetrazine Rings Condensed with Heterocycles 171

A. Condensed through Two Carbon Atoms 171

(1) Condensed with 1,4-Pyrone 171

(2) Condensed with 1,2,3-Triazole 171

B. Condensed through a Carbon Atom and a Nitrogen Atom 173

(1) Condensed with Piperidine 173

(2) Condensed with 1,2,4-Triazole 174

Bibliography 175

IV. The 1,2,3,5- Tetrazines 177
By John G. Erickson

Bibliography 178

V. The 1,2,4,5-Tetrazines 179
By Paul F. Wiley

Introduction 179

1. Uncondensed s-Tetrazines 182

A. Mononuclear s-Tetrazines 182

(1) s-Tetrazines and Hydro Derivatives 182

(2) Substituted s-Tetrazines and Hydro Derivatives 186

B. Polynuclear Uncondensed s-Tetrazines 207

(1) Aliphatic Carbocydic Rings Coupled Directly to s-Tetrazines 207

(2) Aromatic Carbocydic Rings Coupled Directly to s-Tetrazines 208

(3) Heterocyclic Rings Coupled Directly to s-Tetrazines 236

(4) Rings Coupled through Carbon Chains to s-Tetrazines 238

2. Condensed s-Tetrazines 244

Bibliography 246

VI. The Pentazines 250
By John G. Erickson

Bibliography 251

Subject Index 253