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Short Paper | Regular issue | Vol 83, No. 2, 2011, pp.357-363
Published online, 13th January, 2011
DOI: 10.3987/COM-10-12096
Regio-Controlled Synthesis of 1,4-Benzothiazinones

Touria Ghailane, Mohammed Saadouni, Said Boukhris, Nouzha Habbadi, Amina Hassikou, Abdelali Kerbal, Bernard Garrigues, and Abdelaziz Souizi*

*Laboratoire de Synthèse Organique, Organométallique et Théorique, Faculté des Sciences, Université Ibn Tofail, B. P 133-Kénitra, Morocco


Regio-controlled cyclization of gem-dicyanoepoxides with 2-aminothiophenol and its hydrochloride to form 1,4-benzothiazine-2-one or 3-one is described. The cyclization is highly regioselective and the reaction of the epoxides with 2-aminothiophenol under neutral reaction condition gave 1,4-benzothiazine-2-one as a sole cyclized product, whereas that with hydrochloride of 2-aminothiophenol afforded 1,4-benzothiazine-3-one predominantly. The regioselectivity resulted from the reaction condition is discussed.