Best synthetic methods. Sub-series: Key systems and functional
groups - Academic Press , 1996. – 175 p.
Synthesis of indole derivatives has been an active field of chemical research for well over a century. Synthetic interest has been driven by the wide range of indole derivatives which occur in nature and by the biological activity of many indole derivatives of both natural and synthetic origin. In this volume I have attempted to illustrate the most widely used of these synthetic methods. The underlying organization is on the basis of the retrosynthetic concept of identifying the bond(s) which are formed in the process. The chapters pertaining to ring construction (1 8) and substitutions (9-14) are focused on particular ring positions. The final two chapters consider indole-specific oxidation reduction reactions and cycloaddition processes.
Even after 30 years of research activity in the field, my personal experience encompasses only a fraction of the methodologies included in the book. I have selected the methods and examples on the basis of utility and reliability as judged by frequency of application in the literature or by indications that specific procedures are especially convenient. I will welcome comments from chemists whose experience, good or bad, will help in recognizing the best of the many methods that are available.
Introduction
Category Ia Cyclizations
Category Ib Cyclizations
Category Ic Cyclizations
Category Ii Cyclizations.
Category IIab Cyclizations.
Category IIac Cyclizations
Indoles by Annelation of Pyrroles
Synthetic Modification of Indoles by Substitution at Nitrogen.
Introduction of Substituents at C2.
Introduction of Substituents at C3
Modification of 3-Alkyl Substituents by Nucleophilic Substitution .
Introduction of the Tryptamine and Tryptophan Side-Chains.
Introduction of Substituents on the Carbocyclic Ring
Selective Reduction and Oxidaiion Reactions
Synthetic Elaboration of Indole Derivatives using Cycloaddition Reactions
Synthesis of indole derivatives has been an active field of chemical research for well over a century. Synthetic interest has been driven by the wide range of indole derivatives which occur in nature and by the biological activity of many indole derivatives of both natural and synthetic origin. In this volume I have attempted to illustrate the most widely used of these synthetic methods. The underlying organization is on the basis of the retrosynthetic concept of identifying the bond(s) which are formed in the process. The chapters pertaining to ring construction (1 8) and substitutions (9-14) are focused on particular ring positions. The final two chapters consider indole-specific oxidation reduction reactions and cycloaddition processes.
Even after 30 years of research activity in the field, my personal experience encompasses only a fraction of the methodologies included in the book. I have selected the methods and examples on the basis of utility and reliability as judged by frequency of application in the literature or by indications that specific procedures are especially convenient. I will welcome comments from chemists whose experience, good or bad, will help in recognizing the best of the many methods that are available.
Introduction
Category Ia Cyclizations
Category Ib Cyclizations
Category Ic Cyclizations
Category Ii Cyclizations.
Category IIab Cyclizations.
Category IIac Cyclizations
Indoles by Annelation of Pyrroles
Synthetic Modification of Indoles by Substitution at Nitrogen.
Introduction of Substituents at C2.
Introduction of Substituents at C3
Modification of 3-Alkyl Substituents by Nucleophilic Substitution .
Introduction of the Tryptamine and Tryptophan Side-Chains.
Introduction of Substituents on the Carbocyclic Ring
Selective Reduction and Oxidaiion Reactions
Synthetic Elaboration of Indole Derivatives using Cycloaddition Reactions