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Paper | Regular issue | Vol 55, No. 7, 2001, pp.1291-1299
Published online, 1st January, 1970
DOI: 10.3987/COM-01-9230
Reaction of 1-Benzenesulfonylindole-2,3-dicarboxylic Anhydride with Wittig Reagents: Synthesis of Pyrrolo[1,2-a]indoles and Cyclopent[b]indole

Yasuyoshi Miki,* Hiroko Hachiken, Atsuko Kawazoe, Yasuhiko Tsuzaki, and Norihide Yanase

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

Abstract

Treatment of 1-benzenesulfonylindole-2,3-dicarboxylic anhydride with methylenetriphenylphosphorane gave the corresponding ylide. After esterification of the carboxyl group and removal of the benzenesulfonyl group of the ylide, the obtained ylide was reacted with aldehydes to yield α,β-unsaturated ketones, which were converted to pyrrolo[1,2-a]indoles. We also examined the reactivity of the anhydride with (carbethoxymethylene)triphenylphosphorane and (carbethoxyethylidene)triphenylphosphorane.