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Chemistry of Heterocyclic Compounds

, Volume 48, Issue 7, pp 997–1005 | Cite as

Synthesis and reactivity of methyl 3-acyl-6-amino-4-aryl-5-cyano-4H-pyran-2-carboxylates

  • V. P. SheverdovEmail author
  • A. Yu. Andreev
  • O. V. Ershov
  • O. E. Nasakin
  • V. A. Tafeenko
  • V. L. Gein
Article

By treating arylidenemalononitriles with methyl 2,4-dioxobutanoates, derivatives of 4H-pyrans - methyl 3-acyl-6-amino-4-aryl-5-cyano-4H-pyran-2-carboxylates - are obtained, which are novel, promising structural components for the synthesis of carbo- and heterocycles. The reactions of these pyrans with sulfuric and hydrochloric acids, acetic anhydride, and alcohols have been studied. Novel methods have been developed for the preparation of substituted derivatives of cyclopentenone, pyrano[2,3-d]-pyrimidine, 5-oxo-3-phenylpentanoic acid, and nicotinic acid nitrile.

Keywords:

cyclopentenones 5-oxopentanoic acid 4H-pyrans pyridines ring opening 

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Copyright information

© Springer Science+Business Media New York 2012

Authors and Affiliations

  • V. P. Sheverdov
    • 1
    Email author
  • A. Yu. Andreev
    • 1
  • O. V. Ershov
    • 1
  • O. E. Nasakin
    • 1
  • V. A. Tafeenko
    • 2
  • V. L. Gein
    • 3
  1. 1.Chuvashia State University named after I. N. UlyanovCheboksaryRussia
  2. 2.M. V. Lomonosov Moscow State UniversityMoscowRussia
  3. 3.Perm’ State Pharmaceutical AcademyPerm’Russia

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