Ward C. Sumpter, Western Kentucky State College, Bowling Green, Kentucky.F. M. Miller, University of Maryland, Baltimore, Maryland.

• I. Indole 1Introduction 1Synthesis of Indole 3Oxidation of Indole 23Tautomerism of Indole 25Sulfonation of Indole 28Halogen Derivatives of Indole 29Alkyl Derivatives of Indole 31Indoline 36Metal Salts of Indole 40Indole Aldehydes 40Acyl Derivatives of Indole 44Condensation of Indoles with Aldehydes 48Indolylmagnesium Halides 50Indole Polymers 61Preparation and Reactions of Gramine 62Carboxylic Acids of the Indole Series 65II. Carbazole 70Introduction 70Preparation of Carbazole 72Graebe-Ullman Synthesis 72Method of Borsche 73Other Methods of Synthesis of Carbazoles 78Nitro Derivatives of Carbazole 81Aminocarbazoles 85Halogen Derivatives of Carbazole 87Carbazolesulfonic Acids 91Reduction of Carbazole 93Oxidation of Carbazole 96Carbazyl Aldehydes and Ketones 97Carbazole Carboxylic Acids 101N-Acyl Carbazoles 104N-Alkyl Carbazoles 105III. Isatin 110Preparation of Isatin 111Properties of Isatin 114Tautomerism 115Reactions of Isatin 116Oxidation and Reduction 116Halogenation and Nitration 118Acylation and Alkylation 120Reactions of the Carbonyl Groups 121Grignard Reagents 121Amine Derivatives 122Miscellaneous Reagents 126Active Methylene Groups 127Biological Activity of Isatin 132Analytical Uses of Isatin 133IV. Oxindole 134Preparation of Oxindoles 134Properties of Oxindoles 138Tautomerism 138Salts 138Reactions of Oxindole 139Reduction 139Halogenation and Nitration 140Condensation Reactions 142Alkylation and Acylation 146Derivatives 148Hydroxyoxindoles 148Dioxindole 1481 -Hydroxyoxindole 151Aminooxindoles 1513, 3-Diaryloxindoles 152V. Isatogens 154VI. Indoxyl 163Introduction 163Synthesis of Indoxyl 163Physical Properties 165Reactions 165Acyl Derivatives of Intloxyl 167Indoxyl Sulfuric Acid 168Indican 168Indoxylic Acid and Indoxyl-2-aldehyde 169VII. Indigo 171Introduction 171Occurrence of Indigo 174Synthesis of Indigo 175Physical Properties of Indigo 178Chemical Properties of Indigo 179Formation of Salts 179Oxidation of Indigo 180Imides and Oximes of Indigo 181Reduction of Indigo 182Halogenated Indigos 184Alkyl and Acyl Derivatives of Indigo 189Preparation of Indigoids 191Isoindigo and Indirubin 192VIII. Natural Products Containing the Indole Nucleus 196Simple Bases 196Gramine 196Donaxarine 197Tryptophan 197Serotonin 199Abrine 200Hypaphorine 200Bufotenines 201Dipterine 202Calabar Alkaloids 203Physostigmine 203Geneserine 207Harmala Alkaloids 208Harmaline, Harmine, and Harmalol 208Harman 213Eleaginine 213Leptocladine 213Calycanthine 214Calycanthidine 216Folicanthine 217Evodia Alkaloids 218Evodiaminu 218Rutecarpine 218Cinchona Alkaloids 220Cinchonamine 221Quinamine 222Yohinzbe hlkaloids 223Yohimbine 224Corynantheine 233Corynantheidine 234Quebracho Alkaloids 234Aspidospermine 234Vallesine 235Quebrachamine 235Calabash Curare Alkaloids 235Alstonilidine 238Gelsemium Alkaloids 240Alslonia Alkaloids 238Alstonine 238Gelsemine 240Sempervirine 242Gelsemicine 244Rauwdfia Alkaloids 244Rauwolscine 245Gcissospevinzrm Alkaloids 247Strychnos Alkaloids 257Strychnine and Rrucine 258α- and β-Colubrine 275Holstiine 275Mold Products 276Cliotoxin 276Melanine; Aminochrom2s 278Minor Alkaloids 279Uncaria Alkaloids 280Ajmaline 244Serpentine 246Geissospermine 247Ergot Alkaloids 248Vomicine 270Strychnospermine 275Chetomin 278Karnassine 28013iogencsis 281Absorption Spectra of Indole I3ascj 284Index 288