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Indoles - Sundberg R.J.

Sundberg R.J. Indoles - Academic press, 1996. - 95 p.
ISBN 0-12-676945-1
Download (direct link): indoles1996.djvu
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Chapter 5. Category I/ Cyclizations..........................................................................................................................................................................................................45
Chapter 6. Category Ilafr Cyclizations....................................................................................................................................................................................49
Chapter 7. Category Ilac Cyclizations................................................................................................................................................................................................53
Chapter 8. Indoles by Annelation of Pyrroles....................................................................................................................................................................79
Chapter 9. Synthetic Modification of Indoles by Substitution at Nitrogen....................................................89
Chapter 10, Introduction of Substituents at C2..................................................................................................................................................................95
Chapter 11. Introduction of Substituents at C3........................................................................................................................................................105
Chapter 12. Modification of 3-Alkyl Substituents by Nucleophilic Substitution....................................119
Chapter 13, Introduction of the Tryptamine and Tryptophan Side-Chains........................................................125
Chapter 14. Introduction of Substituents on the Carbocyclic Ring..............................................................................135
Chapter 15. Selective Reduction and Oxidation Reactions......................................................................................................................145
Chapter 16 Synthetic Elaboration of Indole Derivatives using Cycloaddition
Reactions......................................................................................................................................................................................................................................................159
Index ..........................................................................................................................................................................................................................................................................................................................................171
V
Dedicated to Wayland E. Nolan in honour of his 70th birthday
Foreword
Best Synthetic Methods is now 10 years old, is a family of 16 volumes and has been well received by the majority of chemists as a valuable aid in their synthetic endeavours, be they academic or commercial. The focus of the series so far has been on special methods, reagents or techniques. This volume is the first of a new sub-series with a focus on heterocycles and their synthesis. It is amazing the extent to which each heterocyclic type has its own specialized synthetic methodology. Whether the chemist is endeavouring to make a heterocycle by ring synthesis or wishes to introduce specific substituents, it is the intention that this new development will serve their needs in a practical, authoritative, fully illustrative and compact manner. Richard Sundberg is an authority on indole chemistry and it is a pleasure to have such a noted heterocyclist to initiate this venture.
O.M.-C.
vii
Preface
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.
Richard J. Sundberg Charlottesville
Detailed Contents
1 Introduction................................................................................................................................................ 1
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