Synthesis and Applicability of Partially Reduced 2- Benzazepines

Authors: Kouznetsov V.; Palma A.; Ewert C.

Source: Current Organic Chemistry, Volume 5, Number 5, May 2001 , pp. 519-551(36)

Publisher: Bentham Science Publishers

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Abstract:

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; acetylcholinesterase; intramolecular nucleophilic substitution; Friedel-Crafts intramolecular acylation; Pictet-Spengler; antiaggregatory; photochemical cyclisation; Clavicipitic acids