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Paper | Regular issue | Vol 83, No. 4, 2011, pp.755-763
Published online, 9th February, 2011
DOI: 10.3987/COM-10-12128
Synthesis of Novel Substituted 4-Hydroxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6,7-dicarbonitriles

Sergey I. Filimonov,* Zhanna V. Chirkova, Igor G. Abramov, Sergey I. Firgang, Galina A. Stashina, and Kyrill Yu. Suponitsky

*Yaroslavl State Technical University, Moscowsky Prospekt 88, 150023 Yaroslavl, Russia

Abstract

New method has been elaborated for synthesis of novel substituted 4-hydroxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6,7-dicarbonitriles by means of activated nucleophilic substitution of the bromine atom in 4-bromo-5-nitrophthalonitrile by treatment of the latter with sodium salts of substituted 3-cyano-2-hydroxy-3-phenyl acrylates followed by reductive cyclisation. The structure of the resulting substituted 4-hydroxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6,7-dicarbonitriles has been determined by single crystal X-ray diffraction analysis.