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Short Paper | Special issue | Vol 90, No. 1, 2015, pp.607-616
Published online, 4th April, 2014
DOI: 10.3987/COM-14-S(K)8
Novel Intramolecular Cyclization-Skeletal Reorganization of 2-Arylthiazoles under Photoirradiation

Noriyoshi Arai,* Moe Mizota, and Takeshi Ohkuma*

*Division of Chemical Process Engineering, Graduate School of Engineering, Hokkaido University, Kita 13 Nishi 8, Kita-ku, Sapporo, Hokkaido 060-8628, Japan

Abstract

Photoirradiation of 2-arylthiazoles derivatives linked with an alkene moiety through a three-atom spacer was investigated. The main products were unexpected tetrahydrofuran-fused thiazepine derivatives with concomitant formation of [2+2] cycloaddition products and regioisomeric thiazoles. The product distribution was little influenced by the reaction conditions and substituents of the substrates.