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Synthesis 2006(15): 2493-2496  
DOI: 10.1055/s-2006-942462
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of 3,3-Disubstituted Isoindolin-1-ones via Iodoamination of α-Substituted Secondary 2-Vinylbenzamides

Kazuhiro Kobayashi*, Masanori Hase, Kenichi Hashimoto, Seiki Fujita, Miyuki Tanmatsu, Osamu Morikawa, Hisatoshi Konishi
Department of Materials Science, Faculty of Engineering, Tottori University, 4-101 Koyama-minami, Tottori 680-8552, Japan
Fax: +81(857)315263; e-Mail: kkoba@chem.tottori-u.ac.jp;
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Publication History

Received 3 March 2006
Publication Date:
04 July 2006 (online)

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Abstract

A new and simple method for the preparation of 3,3-di­substituted isoindolin-1-ones from α-substituted 2-bromostyrenes is described. Construction of the isoindolin-1-one skeleton was accomplished by treating α-substituted secondary 2-vinylbenzamides, easily obtainable from the reaction of α-substituted 2-lithiostyrenes with isocyanates, with iodine to afford 3-substituted 3-iodomethylisoindolin-1-ones.

Key words

iodocyclization - isocyanate - isoindoline - 2-lithio­styrene - secondary benzamide

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