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Synthesis 2001(11): 1693-1703
DOI: 10.1055/s-2001-16763
PAPER
© Georg Thieme Verlag Stuttgart · New York

New Bis-indolic Macrolactams

Jacques Hénin, Eric Noé, Jean-Yves Laronze*
Laboratoire de Chimie Thérapeutique, UMR-CNRS 6013, IFR n°53 Biomolécules, UFR de Pharmacie, 3 Avenue du Maréchal Juin, 51096 Reims Cedex, France
Fax: +33(3)26918029; e-Mail: jy.laronze@univ-reims.fr;
Further Information

Publication History

Received 19 February 2001
Publication Date:
12 August 2004 (online)

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Abstract

Treatment of several ω-halogenoamides, derived from tryptamine, with powdered potassium hydroxide in 1,2-dimethoxyethane in the presence of 18-crown-6, resulted in intramolecular and/or bimolecular cyclization, depending on the length of the chain and dilution conditions, to give macrocyclic compounds. Some of them were converted by a Bischler-Napieralski reaction, followed or not by reduction, to new tetracyclic derivatives of β-carbolines.

Key words

indoles - macrocycles - crown ether - β-carbolines - high dilution

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