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Paper | Regular issue | Vol 55, No. 8, 2001, pp.1455-1466
Published online, 1st January, 1970
DOI: 10.3987/COM-01-9223
■ Indoles XIV. 4-Phenylpyrido[4,3-b]indoles and 5-Phenylazepino[4,5-b]indoles by Cyclisation of N-Indolylalkyl-ephedrine Derivatives — Scope and Stereoselectivity

Michael Decker, Rüdiger Faust, Maike Wedig, Martin Nieger, Ulrike Holzgrabe, and Jochen Lehmann*

*Institute of Pharmacy, University of Bonn, An der Immenburg 4, D-53121 Bonn, Germany

Abstract

4-Phenyltetrahydropyrido[4,3-b]indoles (1) and 5-phenylhexahydro-azepino[4,5-b]indoles (2) were obtained by cyclisation reactions starting from N-3-indolylmethylephedrines and N-3-indolylethylnorephedrines respectively, using conc. sulfuric acid (for 1) and PPA (for 2), the latter cyclisation yielding to the racemised azepinoindoles (2), whereas the previous one reacts to 1 in a remarkably stereoselective manner with double inversion = retention of its configuration, obviously going through a spirocyclic intermediate.