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Note | Regular issue | Vol 75, No. 5, 2008, pp.1225-1231
Published online, 5th February, 2008
DOI: 10.3987/COM-07-11304
Synthesis of 2,4-Disubstituted Isoquinolin-1(2H)-ones Based on Reactions of α-Substituted 2-Lithio-β-methoxystyrenes with Isocyanates

Kazuhiro Kobayashi,* Kazutaka Hayashi, Changeng Nam, Shuhei Fukamachi, 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 preparation of 2,4-disubstituted isoquinolin-1(2H)-ones is described. The reaction of α-substituted 2-lithio-β-methoxystyrenes, generated by treating α-substituted 2-bromo-β-methoxystyrenes with butyllithium, with isocyanates yields the corresponding α-substituted 2-(2-methoxyvinyl)benzamide derivatives, which in turn are transformed into 2,4-disubstituted isoquinolin-1(2H)-ones on treatment with a catalytic amount of concentrated hydriodic acid.