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Note | Regular issue | Vol 71, No. 8, 2007, pp.1827-1835
Published online, 18th May, 2007
DOI: 10.3987/COM-07-11072
A Facile Synthesis of 1,1-Disubstituted Isoindoline Derivatives by Intramolecular Iodoamination of 2-Vinylbenzylamine Derivatives

Kazuhiro Kobayashi,* Shizuka Kondo, Kenichi Hashimoto, Shuhei Fukamachi, Osamu Morikawa, and Hisatoshi Konishi

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

Abstract

The intramolecular iodoamination of N-(2-vinylbenzyl)acetamide derivatives, derived from α-substituted 2-vinylbenzonitriles in two steps, afforded the corresponding 2-acetyl-1-iodomethylisoindoline derivatives, which were transformed into the1-methyl or 1-sulfenylmethyl derivatives by tributyltin hydride reduction or substitution by sodium thiolates, respectively, in reasonable yields.