Abstract
An efficient procedure was developed for the synthesis of previously unknown 3-aryl(styryl)-2-(4-arylthiazol-2-yl)oxirane-2-carboxamides and 2-(4-arylthiazol-2-yl)-1-oxaspiro[2.5]octane-2-carboxamides based on treatment of (E)-3-aryl-2-(4-arylthiazol-2-yl)acrylonitriles and cyclohexylidene(4-arylthiazol-2-yl)acetonitriles with an H2O2—KOH system in EtOH. Oxidation of (E)-3-(4-chlorophenyl)-2-(4-phenylthiazol-2-yl)acrylonitrile with an H2O2—AcOH system affords 3-(4-chlorophenyl)-2-(4-phenylthiazol-2-yl)oxirane-2-carbonitrile in 55% yield.
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 2319–2322, October, 2005.
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Dotsenko, V.V., Krivokolysko, S.G. & Litvinov, V.P. Oxidation of 2-(thiazol-2-yl)acrylonitrile derivatives with an H2O2—KOH system: Convenient route to new oxirane-2-carboxamides. Russ Chem Bull 54, 2394–2397 (2005). https://doi.org/10.1007/s11172-006-0128-z
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DOI: https://doi.org/10.1007/s11172-006-0128-z