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Note | Regular issue | Vol 75, No. 9, 2008, pp.2301-2307
Published online, 28th April, 2008
DOI: 10.3987/COM-08-11399
Synthesis of 1,4-Dihydro-2H-3,1-benzoxazin-2-ones by Hydriodic Acid Mediated Cyclization of tert-Butyl 2-Vinylphenylcarbamates

Kazuhiro Kobayashi,* Shuhei Fukamachi, and Hisatoshi Konishi

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


A two-step facile synthesis of 4,4-disubstituted 1,4-dihydro-2H-3,1- benzoxazin-2-ones starting from ±-substituted 2-aminostyrenes is described. The method involves the hydriodic acid mediated cyclization of t-butyl 2-vinylphenylcarbamate derivatives, which could be easily prepared by N-t-butoxycarbonylation of ±-substituted 2-aminostyrene derivatives, under mild conditions.