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Chemistry of Heterocyclic Compounds

, Volume 48, Issue 2, pp 309–319 | Cite as

On the regioselectivity of the reaction of cyanothioacetamide with 2-acetylcyclo-hexanone, 2-acetylcyclopentanone, and 2-acetyl-1-(morpholin-4-yl)-1-cycloalkenes

  • V. V. DotsenkoEmail author
  • S. G. Krivokolysko
  • V. V. Polovinko
  • V. P. Litvinov
Article

It has been established that the interaction of cyanothioacetamide with 2-acetylcyclohexanone, 2-acetylcyclopentanone, or their enamines (2-acetyl-1-(morpholin-4-yl)-1-cycloalkenes) contrary to the literature data have a non-regiospecific character and leads to the formation of mixtures of 3-cyano-4-methyl-5,6-tri(tetra)methylenepyridine-2(1 H)-thiones and 3-cyano-6-methyl-4,5-tri(tetra)methylene-pyridine-2(1 H)-thiones with a predominance of the latter.

Keywords

2-acetylcyclohexanone 2-acetylcyclopentanone cyanothioacetamide Guareschi-Thorpe reaction regioselectivity 

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Copyright information

© Springer Science+Business Media, Inc. 2012

Authors and Affiliations

  • V. V. Dotsenko
    • 1
    Email author
  • S. G. Krivokolysko
    • 1
  • V. V. Polovinko
    • 2
  • V. P. Litvinov
    • 3
  1. 1.“ChemEx” LaboratoryVladimir Dal’ East-Ukrainian National UniversityLuganskUkraine
  2. 2.Enamine LtdKievUkraine
  3. 3.N. D. Zelinsky Institute of Organic ChemistryRussian Academy of SciencesMoscowRussia

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