Advances in Heterocyclic Chemistry (eBook)

Cover 1
Advances in Heterocyclic Chemistry, Volume 3 4
Copyright Page 5
Contents 10
Contributors 6
Preface 8
Contents of Volume 1 12
Contents of Volume 2 13
Errata 14
Chapter 1. The Quaternization of Heterocyclic Compounds 16
I. Introduction 17
II. Reagents for Quaternization 17
III. The Influence of Substituents in Mono-N-Heterocyclyls 26
IV. The Position of Quaternization in Monocyclic Compounds 31
V. The Position of Quaternization in Compounds with Two or More Nitrogen-Containing Rings 53
VI. Reaction at Atoms Other Than Nitrogen 66
VII. The Mechanism of Quaternization 68
Chapter 2. The Reactions of Heterocyclic Compounds with Carbenes 72
I. Introduction 72
II. Reactions with Five-Membered Heterocyclic Rings 78
III. Reactions with Six-Membered Heterocyclic Rings 88
Chapter 3. The Carbolines 94
I. Introduction 94
II. Nomenclature 95
III. Synthesis 98
IV. Reactions of the Carbolines 157
V. Ring Extension 191
VI. Properties and Structure of the Anhydro-Bases 198
VII. Biogenesis and Biosynthesis of Naturally Occurring Carbolines 210
VIII. Spectra 217
Chapter 4. Applications of the Hammett Equation to Heterocyclic Compounds 224
I. Introduction 224
II. Substituent Constants for Heteroatoms 230
III. Reactions at the Heteroatom and at Side-Chains Attached Thereon 238
IV. Transmission of Substituent Effects through Heterocyclic Systems 251
V. Polycyclic Compounds 258
VI. Tautomeric Equilibria 271
VII. Appendix : Analysis of Variance 276
Chapter 5. 1,2,3,4-Thiatriazoles 278
I. Introduction 278
II. Synthesis and Chemical Properties of 1,2,3,4-Thiatriazoles 280
III. 1,2,3,4-Thiatriazoles Substituted with C-Radicals 282
IV. 1,2,3,4-Thiatriazole-5-thiol and Its Derivatives 284
V. 5-Alkoxy-1,2,3,4-thiatriazoles 292
VI. 5-Substituted-amino-1,2,3,4-thiatriazoles 292
Chapter 6. Nucleophilic Heteroaromatic Substitution 300
I. Introduction 300
II. Course and Kinetic Form of the Reactions 305
III. Reagent and Solvent Effects 316
IV. The Reactivityof the Heterocyclic Substrate 331
V. A General Comment on Mechanism 367
VI. Inorganic Heteroaromatic Substitution Reactions 372
VII. Appendix: Kinetic Data for Nucleophilic Heteroaromatic Substitution 374
Chapter 7. Pentazoles 388
I. Introduction 388
II. The Characterization of Arylpentazoles 389
III. The Formation and Decomposition of Arylpentazoles 393
Author Index 400
Subject Index 422