Heterocyclic Compounds with Indole and Carbazole Systems, Volume 8: (Chemistry of Heterocyclic Compounds: A Series Of Monographs)

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.

Table of Contents:
I. Indole 1 Introduction 1 Synthesis of Indole 3 Oxidation of Indole 23 Tautomerism of Indole 25 Sulfonation of Indole 28 Halogen Derivatives of Indole 29 Alkyl Derivatives of Indole 31 Indoline 36 Metal Salts of Indole 40 Indole Aldehydes 40 Acyl Derivatives of Indole 44 Condensation of Indoles with Aldehydes 48 Indolylmagnesium Halides 50 Indole Polymers 61 Preparation and Reactions of Gramine 62 Carboxylic Acids of the Indole Series 65 II. Carbazole 70 Introduction 70 Preparation of Carbazole 72 Graebe-Ullman Synthesis 72 Method of Borsche 73 Other Methods of Synthesis of Carbazoles 78 Nitro Derivatives of Carbazole 81 Aminocarbazoles 85 Halogen Derivatives of Carbazole 87 Carbazolesulfonic Acids 91 Reduction of Carbazole 93 Oxidation of Carbazole 96 Carbazyl Aldehydes and Ketones 97 Carbazole Carboxylic Acids 101 N-Acyl Carbazoles 104 N-Alkyl Carbazoles 105 III. Isatin 110 Preparation of Isatin 111 Properties of Isatin 114 Tautomerism 115 Reactions of Isatin 116 Oxidation and Reduction 116 Halogenation and Nitration 118 Acylation and Alkylation 120 Reactions of the Carbonyl Groups 121 Grignard Reagents 121 Amine Derivatives 122 Miscellaneous Reagents 126 Active Methylene Groups 127 Biological Activity of Isatin 132 Analytical Uses of Isatin 133 IV. Oxindole 134 Preparation of Oxindoles 134 Properties of Oxindoles 138 Tautomerism 138 Salts 138 Reactions of Oxindole 139 Reduction 139 Halogenation and Nitration 140 Condensation Reactions 142 Alkylation and Acylation 146 Derivatives 148 Hydroxyoxindoles 148 Dioxindole 148 1 -Hydroxyoxindole 151 Aminooxindoles 151 3, 3-Diaryloxindoles 152 V. Isatogens 154 VI. Indoxyl 163 Introduction 163 Synthesis of Indoxyl 163 Physical Properties 165 Reactions 165 Acyl Derivatives of Intloxyl 167 Indoxyl Sulfuric Acid 168 Indican 168 Indoxylic Acid and Indoxyl-2-aldehyde 169 VII. Indigo 171 Introduction 171 Occurrence of Indigo 174 Synthesis of Indigo 175 Physical Properties of Indigo 178 Chemical Properties of Indigo 179 Formation of Salts 179 Oxidation of Indigo 180 Imides and Oximes of Indigo 181 Reduction of Indigo 182 Halogenated Indigos 184 Alkyl and Acyl Derivatives of Indigo 189 Preparation of Indigoids 191 Isoindigo and Indirubin 192 VIII. Natural Products Containing the Indole Nucleus 196 Simple Bases 196 Gramine 196 Donaxarine 197 Tryptophan 197 Serotonin 199 Abrine 200 Hypaphorine 200 Bufotenines 201 Dipterine 202 Calabar Alkaloids 203 Physostigmine 203 Geneserine 207 Harmala Alkaloids 208 Harmaline, Harmine, and Harmalol 208 Harman 213 Eleaginine 213 Leptocladine 213 Calycanthine 214 Calycanthidine 216 Folicanthine 217 Evodia Alkaloids 218 Evodiaminu 218 Rutecarpine 218 Cinchona Alkaloids 220 Cinchonamine 221 Quinamine 222 Yohinzbe hlkaloids 223 Yohimbine 224 Corynantheine 233 Corynantheidine 234 Quebracho Alkaloids 234 Aspidospermine 234 Vallesine 235 Quebrachamine 235 Calabash Curare Alkaloids 235 Alstonilidine 238 Gelsemium Alkaloids 240 Alslonia Alkaloids 238 Alstonine 238 Gelsemine 240 Sempervirine 242 Gelsemicine 244 Rauwdfia Alkaloids 244 Rauwolscine 245 Gcissospevinzrm Alkaloids 247 Strychnos Alkaloids 257 Strychnine and Rrucine 258 α- and β-Colubrine 275 Holstiine 275 Mold Products 276 Cliotoxin 276 Melanine; Aminochrom2s 278 Minor Alkaloids 279 Uncaria Alkaloids 280 Ajmaline 244 Serpentine 246 Geissospermine 247 Ergot Alkaloids 248 Vomicine 270 Strychnospermine 275 Chetomin 278 Karnassine 280 13iogencsis 281 Absorption Spectra of Indole I3ascj 284 Index 288

About the Author :
W. C. Sumpter is the editor of Heterocyclic Compounds with Indole and Carbazole Systems, Volume 8, published by Wiley. F. M. Miller is the editor of Heterocyclic Compounds with Indole and Carbazole Systems, Volume 8, published by Wiley.