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Modifications to the Vilsmeier‐Haack formylation of 1,4‐dimethylcarbazole and its application to the synthesis of ellipticines
Author(s) -
Deane Fiona M.,
Miller Charlotte M.,
Maguire Anita R.,
McCarthy Florence O.
Publication year - 2011
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.598
Subject(s) - formylation , chemistry , yield (engineering) , combinatorial chemistry , organic chemistry , catalysis , materials science , metallurgy
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).