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Paper | Regular issue | Vol 45, No. 7, 1997, pp.1363-1384
Published online, 1st January, 1970
DOI: 10.3987/COM-97-7820
Synthetic Approaches to Benzofuran Containing Insulin Sensitivity Enhancer Compounds for Treatment of Type II Diabetes

Bret E. Huff, Cindy L. Leffelman, Michael E. LeTourneau, Kevin A. Sullivan, Jeffrey A. Ward, and John R. Stille*

*Chemical Process Research and Development Division, Lilly Reserach Laboratories, Eli Lilly & Company, Lilly Corporate Center, Indianapaolis, IN 46285-4813, U.S.A.

Abstract

The search for Insulin Sensitivity Enhancer (ISE) compounds, for potential use in the treatment of Type II diabetes, has led to the synthesis of compounds that contain a benzofuran spacer between an aryloyl substituent and a 2,4-thiazolidinedione pharmacophore. Sequential combination of haloacetyl aryl substrates with 5-formylsalicylaldehyde gave the desired 2-aryloyl-5-formylbenzofuran intermediates. A related class of compounds, those with a methylene tether between the aromatic moiety and the benzofuran spacer, were also prepared through this strategy.