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Modifications to the Vilsmeier-Haack formylation of 1,4-dimethylcarbazole and its application to the synthesis of ellipticines

✍ Scribed by Fiona M. Deane; Charlotte M. Miller; Anita R. Maguire; Florence O. McCarthy

Publisher: Journal of Heterocyclic Chemistry
Year: 2011
Tongue: English
Weight: 192 KB
Volume: 48
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.598

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✦ Synopsis

Abstract

An improved method for the preparation of 3‐formyl‐1,4‐dimethylcarbazole, a key intermediate in the synthesis of ellipticine, is presented. Conditions of the Vilsmeier‐Haack reaction have been modified to facilitate the production of 3‐formyl‐1,4‐dimethylcarbazole as a major product leading to an overall improvement in yield of ellipticine from 3% to 14%. This approach was also applied to the synthesis of 6‐methylellipticine and 9‐methoxyellipticine. J. Heterocyclic Chem., (2011).

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