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Russian Chemical Bulletin

, Volume 54, Issue 10, pp 2394–2397 | Cite as

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

  • V. V. Dotsenko
  • S. G. Krivokolysko
  • V. P. Litvinov
Article

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.

Key words

α,β-unsaturated nitriles oxidation hydrogen peroxide Radziszewski reaction oxirane-2-carboxamides 1-oxaspiro[2.5]octane-2-carboxamides oxirane-2-carbonitriles 

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Copyright information

© Springer Science+Business Media, Inc. 2005

Authors and Affiliations

  • V. V. Dotsenko
    • 1
  • S. G. Krivokolysko
    • 1
  • V. P. Litvinov
    • 2
  1. 1.V. Dal East Ukrainian National UniversityLuganskUkraine
  2. 2.N. D. Zelinsky Institute of Organic ChemistryRussian Academy of SciencesMoscowRussian Federation

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