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Paper | Regular issue | Vol 53, No. 10, 2000, pp.2143-2149
Published online, 1st January, 1970
DOI: 10.3987/COM-00-8950
Reaction of 3-Ethoxycarbonylindolizine-1,2-dicarboxylic Anhydride: Synthesis of 2-Acylindolizines and Quinones

Yasuyoshi Miki,* Noriko Nakamura, Ryota Yamakawa, Hiroko Hachiken, and Ko-ichi Matsushita

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

Abstract

Reaction of indolizine-1,2-dicarboxylic anhydride with Grignard reagents gave 2-acylindolizine-1-carboxylic acids, which were converted to 2-acylindolizines. The anhydride reacted with anisole in the presence of titanium chloride(IV) to afford 2-(4-methoxybenzoyl)indolizine-1-carboxylic acid, which was also led to 2-(4-methoxybenzoyl)indolizine. Successive treatment of the 2-acylindolizine-1-carboxylic acids with phosphorus pentachloride and aluminum(III) chloride provided the corresponding quinones.