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Note | Regular issue | Vol 57, No. 7, 2002, pp.1293-1297
Published online, 1st January, 1970
DOI: 10.3987/COM-02-9486
Syntheses of 3-Acylindoles via the Alkylation of the Dianion of 3-Acetylindole

Jeffrey H. Byers* and Yong Zhang

*Department of Chemistry and Biochemistry, Middlebury College, Middlebury, VT 05753, U.S.A.

Abstract

The dianion of 3-acetylindole can be generated upon sequential treatment with NaH and n-BuLi. This dianion can be C-alkylated at the acetyl methyl group with high regioselectivity, leading to efficient syntheses of 3-acylindoles. Addition of excess electrophile leads to a dialkylated product.