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 andTryptophan Side-Chains. Introduction of the Substituents on the Carbocyclic Ring. Selective Reduction and Oxidation Reactions. Synthetic Elaboration for Indole Derivatives using Cycloaddition Reactions. Subject Index.
Indoles continue to be of great interest to the pharmaceutical industry and at the current time several thousand specific new derivatives are reported annually. Research has been driven by the wide range of indole derivatives which occur in nature and through the biological activity of many indole derivatives, of both natural and synthetic origin.This book provides a systematic guide to the most useful and important reactions in the field for both synthesis and synthetic modification of the indole ring. While including the most recently developed and promising methods, it also updates informationavailable on classical methods to give the reader an up-to-date and comprehensive view of the subject. The methods are illustrated by procedures drawn from the literature and by tables including examples chosen to indicate both the scope of applicabilityand variations in methodology. The organization of the book is based on the retrosynthetic concept of identifying the bond(s) formed in the reaction, which in turn identifies potential starting materials.
- Includes systematic summaries of the most important methods for the construction of indoles from aromatic precursors
- Discusses methods for preparing indoles by annelation of pyrroles
- Covers methods for adding or modifying substituent groups, including methods for introducing the tryptamine and tryptophan side-chainsExamines reduction/oxidation reactions that are specific for indoles
- Considers use of cycloaddition reactions for synthetic elaboration of indoles
Synthetic chemists in academia and industry
- No. of pages:
- © Academic Press 1996
- 28th May 1996
- Academic Press
- eBook ISBN:
- Hardcover ISBN:
"This volume is a valuable addition to the Best synthetic methods series, and the author and publishers are to be congratulated on producing a book that all concerned with nitrogen heterocyclic chemistry will find of considerable value." --CHEMISTRY AND INDUSTRY
"In his preface, Professor Sundberg states that he attempted to illustrate the most widely used synthetic methods in indole chemistry on the basis of the retrosynthetic concept of identifying the bonds being formed. Not only has he succeeded, but he hasdone an outstanding job...the book is an absolute must for those interested in indole chemistry...(it) describes most major classical methods and emphasizes all the newer methods available. Professor Sundberg is to be congratulated." --JOURNAL OF MEDICINAL CHEMISTRY
Alan Katritzky was educated at Oxford and has held faculty positions at Cambridge and East Anglia before he migrated in 1980 to the University of Florida, where he was Kenan Professor and Director for the Institute for Heterocyclic Compounds. During his career he has trained more than 1000 graduate students and post-docs, and lectured and consulted world-wide. He led the team, which produced “Comprehensive Heterocyclic Chemistry” and its sequels, "CHEC-II" and "CHEC-III”, has edited “Advances in Heterocyclic Chemistry, Vols. 1 through 111” and conceived the plan for “Comprehensive Organic Functional Group Transformations”. He founded Arkat-USA, a non-profit organization which publishes “Archive for Organic Chemistry” (ARKIVOC) an electronic journal completely free to authors and readers at (www.arkat-usa.org). Honors include 14 honorary doctorates from 11 countries and membership of foreign membership of the National Academies of Britain, Catalonia, India, Poland, Russia and Slovenia.
Department of Chemistry, University of Florida, Gainesville, USA
University of Sunderland, UK
Imperial College of Science and Technology, London, UK
Richard J. Sundberg has been a member of the chemistry department at the University of Virginia since 1964. His research has included both development of synthetic methods for indoles and other heterocycles. The scope of his research also extends into the synthesis of biologically active compounds, including natural products such as the vinca alkaloids.
The University of Virginia