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Synthesis 2010(22): 3849-3854  
DOI: 10.1055/s-0030-1258282
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Versatile Synthesis of 3-Substituted 4-Cyano-1,2,3,4-tetrahydro-1-oxo-β-carbolines

Kilian Huber, Oliver Kast, Franz Bracher*
Department of Pharmacy, Center for Drug Research, Ludwig-Maximilians University Munich, Butenandtstrasse 5-13, 81377 Munich, Germany
Fax: +49(89)218077171; e-Mail: franz.bracher@cup.uni-muenchen.de;
Further Information

Publication History

Received 28 June 2010
Publication Date:
01 October 2010 (online)

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Abstract

In a project aimed at the synthesis of analogues of the cytotoxic β-carboline alkaloid bauerine C with more advantageous solubility properties, a 3-amino analogue was prepared by treating ethyl 3-(cyanomethyl)indole-2-carboxylate with ammonia. Upon addition of aldehydes or ketones to the reaction mixture, 3-substituted 4-cyano-1,2,3,4-tetrahydro-1-oxo-β-carbolines were obtained in a one-pot condensation. When cyclic ketones are used, the procedure allows a convenient synthesis of tetracyclic spiro compounds.

Key words

β-carbolines - cyclizations - multicomponent reactions - indoles - lactams

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