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ISSUE 10

Year 2005, Month 10 (Section Full Articles, Page 2394)

Oxidation of 20-(thiazol-2-yl)acrylonitrile derivatives with an H2O2—KOH system: convenient route to new oxirane-2-carboxamides

V. V. Dotsenko (a), S. G. Krivokolysko (a), and V. P. Litvinov (b)

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]oc-tane-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-2yl)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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