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Heterocyclic Compounds with Indole and Carbazole Systems, Volume 8

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Heterocyclic Compounds with Indole and Carbazole Systems, Volume 8

W. C. Sumpter, F. M. Miller

ISBN: 978-0-470-18807-1 September 2009 319 Pages

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Description

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.

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