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Paper | Regular issue | Vol 78, No. 3, 2009, pp.669-677
Published online, 5th November, 2008
DOI: 10.3987/COM-08-11554
Synthesis of 1H-Isoindol-3-amine Derivatives by Iodine-Mediated Cyclization of 2-Vinylbenzamidine Derivatives

Kazuhiro Kobayashi,* Mai Horiuchi, Shuhei Fukamachi, and Hisatoshi Konishi

*Department of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, 4-101 Koyama-minami, Tottori 680-8552, Japan

Abstract

It has been found that the reaction of 2-vinylbenzamidine derivatives, prepared by reacting 2-vinylbenzonitriles with lithium cyclic secondary amides, with iodine in the presence of sodium hydrogen carbonate in acetonitrile resulted in the formation of the corresponding 1-iodomethyl-1H-isoindole-3-amine derivatives in reasonable overall yields based on the starting 2-vinylbenzonitriles. We have also found that transformation of these 1-iodomethyl derivatives into 1-sulfenylmethyl derivatives could be achieved in good yields on treatment with various sodium thiolates.