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Paper | Regular issue | Vol 89, No. 12, 2014, pp.2729-2738
Published online, 10th December, 2014
DOI: 10.3987/COM-14-13127
Synthesis of 2-Aryl-(Z)-4-(halomethylidene)-4H-3,1-benzoxazines by Sodium Hydride Mediated Cyclization of N-[2-(2,2-Dihaloethenyl)phenyl]arenecarboxamides

Kazuhiro Kobayashi,* Ippei Nozawa, and Daiki Kado

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


A simple two-step procedure for the preparation of 2-aryl-(Z)-4-(halomethylidene)-4H-3,1-benzoxazines from readily available 2-(2,2- dihaloethenyl)benzenamines is developed. Thus, these amines were N-aroylated with the respective aroyl chloride to give N-[2-(2,2- dihaloethenyl)phenyl]arenecarboxamides, which in turn were treated with sodium hydride to afford the desired products.