The Chemistry of Indoles

PrefaceList of Abbreviations I. Electrophilic Substitution Reactions on the Indole Ring A. Introduction to the Structure and Reactivity of Indoles B. Protonation of Indoles C. Nitration D. Halogenation E. Azo Coupling Reactions and Reactions with Azides F. Sulfonation G. Alkylation of Indoles and Metalloindoles with Alkyl Halides and Related Alkylating Agents H. Reactions with Carbenes I. Acylation of Indoles and Metalloindoles J. Reactions with Ketones and Aldehydes K. Reactions with Iminium Bonds L. Reactions with Electron Deficient Olefins, Acetylenes, and Quinones M. Miscellaneous Electrophilic Substitutions N. The Mechanism of Electrophilic Substitution in 3-Substituted Indoles 0. Theoretical Treatment of Indole Reactivity and Substituent Effects References II. General Reactions of Functionally Substituted Indoles A. Introduction B. Substitution and Elimination Reactions at Indolylcarbinyl Carbon Atoms C. Hydrogenolysis of Indolylcarbinyl Substituents D. Cleavage of Substituents from the Indole Ring. Decarboxylations and Related Reactions E. Reactions of 3H-Indole Derivatives F. Reactions of Vinylindoles G. Reduction of the Indole Ring and Interconversion of Indoles and Dihydroindoles(Indolines) H. The Indoline-Indole Synthetic Method I. Metalation of Indoles References III. Synthesis of the Indole Ring A. The Fischer Indole Synthesis B. Synthesis of Indoles from Derivatives of α-Anilinoketones: The Bischler Synthesis C. Indoles from the Reactions of Enamines with Quinones: The Nenitzescu Synthesis D. Reductive Cyclizations E. Electrophilic Cyclization of Styrene Derivatives F. The Madelung Synthesis G. Oxidative Cyclizations H. Miscellaneous Reactions Leading to Indole Ring Formation References IV. Synthetic Elaboration of the Indole Ring A. Synthetic Approaches to Indolealkanoic Acids B. Synthesis of Derivatives of Tryptamine C. Synthesis of Tryptophan and Its Derivatives D. Synthesis of Derivatives of ß-Carboline E. Synthesis of Indole Alkaloids ReferencesV. Oxidation, Degradation, and Metabolism of the Indole Ring A. The Reactions of Indoles with Molecular Oxygen and Peroxides B. Ozonolysis of Indoles C. Oxidation of Indoles with Other Oxidizing Agents D. Oxidation of Indole Derivatives in Biological Systems and Chemical Models of Biological Systems ReferencesVI. Rearrangement, Ring Expansion, and Ring Opening Reactions of Indoles A. Simple Substituent Migrations B. Rearrangements of Indolinones and Indolinols C. Ring Expansions and Ring Opening Reactions of Indoles ReferencesVII. Hydroxyindoles and Derivatives Including Oxindole, 3-Indolinone, and Isatin A. Reactions of Oxindoles B. Synthesis of the Oxindole Ring C. Derivatives of 3-Hydroxyindole and 3-Indolinone (Indoxyls) D. Synthesis of 3-Indolinone Derivatives E. Indoles with Carbocyclic Hydroxyl Substituents F. 1-Hydroxyindoles G. 2,3-Indolinedione (Isatin) Derivatives H. 3H-Indole-3-One-1 -Oxides (Isatogens) References VIII. Aminoindoles Text References IX. Ketones, Aldehydes, and Carboxylic Acids Derived from Indole A. Ketones and Aldehydes Derived from Indole B. Synthesis of Indolyl Ketones and Indolecarboxaldehydes C. Indolecarboxylic Acids ReferencesX. Naturally Occurring Derivatives of Indole and Indoles of Physiological and Medicinal Significance A. Introduction B. Indole-Derived Antibiotics C. Indoles of Physiological Significance: Tryptophan, Serotonin, and Melatonin D. Indole Derivatives as Hallucinogens E. Medicinally Significant Indoles F. Luciferins Derived from Indole G. Miscellaneous Indole Conjugates and Metabolites References Author IndexSubject Index