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Current Organic Chemistry


ISSN (Print): 1385-2728
ISSN (Online): 1875-5348

Synthesis and Applicability of Partially Reduced 2- Benzazepines

Author(s): Vladimir Kouznetsov, Alirio Palma and Claude Ewert

Volume 5, Issue 5, 2001

Page: [519 - 551] Pages: 33

DOI: 10.2174/1385272013375391

Price: $65


This review covers recent developments in the area of partially reduced 2-benzazepines, particularly synthesis and their main applications. The first chapter discusses the principal routes (ring-closure methods with formation of C-N or C-C bonds as well as ring expansion methods) to obtain these heterocycles. The second chapter covers total syntheses of the alkaloids galanthamine, lycoramine, narwedine and clavicipitic acid which all contain the 2-benzazepine core structure. At the end of the chapter, approaches to the homoberbine and ribasine skeleton are given. Additional information is provided for synthesis of medicinally important 8,9-dichloro-2,3,4,5-tetrahydro- 1H-2-benzazepine.

Keywords: 2- Benzazepines, alkaloids galanthamine, Tetrahydrobenzazepines, acetylcholinesterase, intramolecular nucleophilic substitution, Friedel-Crafts intramolecular acylation, Pictet-Spengler, antiaggregatory, photochemical cyclisation, Clavicipitic acids

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