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Paper | Regular issue | Vol 57, No. 9, 2002, pp.1635-1643
Published online, 1st January, 1970
DOI: 10.3987/COM-02-9537
Synthesis of 2- and 3-Benzoylindoles by Friedel-Crafts Reaction of Indole-2,3-dicarboxylic Anhydrides with Anisoles

Yasuyoshi Miki,* Yasuhiko Tsuzaki, Chika Kai, and Hiroko Hachiken

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

Abstract

Reaction of 1-benzylindole-2,3-dicarboxylic anhydride with anisole in the presence of titanium(IV) chloride gave 2-(4-methoxybenzoyl)indole-3-carboxylic acid as the sole product. However, 1-benzenesulfonylindole-2,3-dicarboxylic anhydride with anisole afforded 3-(4-methoxybenzoyl)indole-2-carboxylic acid. These carboxylic acids could be converted to the corresponding benzoylindoles.