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Note | Regular issue | Vol 75, No. 7, 2008, pp.1779-1788
Published online, 18th March, 2008
DOI: 10.3987/COM-08-11359
Synthesis of 1H-Isoindoles by Iodoamination of 2-Vinylbenzylidenamines

Kazuhiro Kobayashi,* Mai Horiuchi, Miyuki Tanmatsu, and Hisatoshi Konishi

*Department of Materials Science, Faculty of Engineering, Tottori University, 4-101 Koyama-minami, Tottori 680-8552, Japan

Abstract

An efficient method for the synthesis of 1H-isoindole derivatives is described. It is based on iodine mediated cyclization of aryl(or alkyl)(2-vinylbenzyliden)amine derivatives, which can be easily prepared from the reactions of 2-lithiostyrene derivatives with various nitriles, furnishing the corresponding iodoamination products, 3-aryl(or alkyl)-1-iodomethyl-1H-isoindole derivatives, in satisfactory overall yields.