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Paper | Regular issue | Vol 45, No. 6, 1997, pp.1143-1150
Published online, 1st January, 1970
DOI: 10.3987/COM-97-7806
Reaction of Indole-2,3-dicarboxylic Anhydride with Grignard Reagents: Synthesis of 2-Acylindoles

Yasuyoshi Miki,* Hiroko Hachiken, and Ichigo Yoshikawa

*Faculty of Pharmaceutical Sciences, Kinki University, 3-4-1, Kowakae, Higashi-Osaka 577-8502, Japan

Abstract

Reaction of indole-2,3-dicarboxylic anhydrode with methylmagnesium bromide and phenylmangesium bromide gave 2-acetyl- and 2-benzoyl-indole-3-carboxylic acids, but with tert-butylmagnesium chloride, 3-pivaloylindole-2-carboxylic acids were obtained as the main products. Treatment of 2-acylindole-3-carboxylic acids with copper chromite in quinoline or potassium hydroxide gave the corresponding 2-acylindoles.