The Chemistry of Indoles - 1st Edition - ISBN: 9780126769500, 9780323147866

The Chemistry of Indoles

1st Edition

Authors: Richard Sundberg
eBook ISBN: 9780323147866
Imprint: Academic Press
Published Date: 28th January 1970
Page Count: 504
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Organic Chemistry, Volume 18: The Chemistry of Indoles discusses the chemistry of indole derivatives. This book explores the potent biological activity of several indole derivatives and explains the structure of indole alkaloids. Organized into 10 chapters, this monograph starts with an overview of the most important types of reactions of the indole ring on a mechanical basis. This text then proceeds to review the methods of synthesizing indoles and describes the oxidations and rearrangements of indole derivatives. Other chapters explore the special features of the synthesis and reactivity of hydroxyindoles, acylindoles, and aminoindoles. This book discusses as well the properties of carboxyl groups, which is substituted on the benzenoid ring of the indole nucleus that is typical of aromatic carboxylic acids. The final chapter deals with the certain classes of indoles that are found in nature. Chemists, researchers, and readers interested in the chemistry of indoles will find this book extremely useful.

Table of Contents


List 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


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


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


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


V. 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


VI. 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


VII. 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)


VIII. Aminoindoles



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


X. 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


Author Index

Subject Index


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Academic Press
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About the Author

Richard Sundberg

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