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Russian Chemical Bulletin

, Volume 56, Issue 7, pp 1431–1436 | Cite as

A new stereoselective synthesis of 2-amino-4,5-dihydrothiophene-3-carbonitrile derivatives

  • V. V. Dotsenko
  • S. G. Krivokolysko
  • A. N. Chernega
  • V. P. Litvinov
Article

Abstract

A new stereoselective method for the synthesis of trans-isomers of 2-amino-4-aryl-5-benzoyl-4,5-dihydrothiophene-3-carbonitriles was proposed. The method involves base-catalyzed reactions of phenacyl thiocyanate with 3-(het)aryl-2-cyanoprop-2-enethioamides. (4R,5S/4S,5R)-2-Amino-5-benzoyl-4-(2-chlorophenyl)-4,5-ihydrothiophene-3-carbonitrile was structurally characterized by X-ray diffraction analysis.

Key words

phenacyl thiocyanate 3-(het)aryl-2-cyanoprop-2-enethioamides cyanothio-acetamide the Michael reaction cyclocondensation X-ray diffraction analysis trans-2-amino-4-(het)aryl-5-benzoyl-4,5-dihydrothiophene-3-carbonitriles 

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Copyright information

© Springer Science+Business Media, Inc. 2007

Authors and Affiliations

  • V. V. Dotsenko
    • 1
  • S. G. Krivokolysko
    • 1
  • A. N. Chernega
    • 2
  • V. P. Litvinov
    • 3
  1. 1.ChemEx LaboratoryV. Dal’ East-Ukrainian National UniversityLuganskUkraine
  2. 2.Institute of Organic ChemistryNational Academy of Sciences of UkraineKievUkraine
  3. 3.N. D. Zelinsky Institute of Organic ChemistryRussian Academy of SciencesMoscowRussian Federation

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