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

…, CM Miller, AR Maguire, FO McCarthy

Index: Deane, Fiona M.; Miller, Charlotte M.; Maguire, Anita R.; McCarthy, Florence O. Journal of Heterocyclic Chemistry, 2011 , vol. 48, # 4 p. 814 - 823

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Citation Number: 5

Abstract

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- ...