Chemistry of Heterocyclic Compounds

, Volume 14, Issue 11, pp 1257–1260 | Cite as

Tautomerism of azine derivatives

III. Tautomerism of substituted 4-pyrimidinylmethanes
  • V. V. Lapachev
  • O. A. Zagulyaeva
  • S. F. Bychkov
  • V. P. Mamaev


The tautomeric properties of 4-pyrimidinylmethanes were studied in the case of 2-CH3- and 2-CF3-4-pyrimidinylcyanoacetic esters, 2-CH3-4-pyrimidinylnitromethane, and 4-pyrimidinylnitromethane. It was shown by 1H and 13C NMR spectroscopy that an equilibrium with the participation of three tautomeric forms — pyrimidine form A and pyrimidinylidene forms B and C with “o- and p-quinoid” orientations of the double bonds in the heteroring — may be realized in aprotic dipolar solvents (dimethyl sulfoxide).


Spectroscopy Ester Organic Chemistry Dimethyl Double Bond 
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Copyright information

© Plenum Publishing Corporation 1979

Authors and Affiliations

  • V. V. Lapachev
    • 1
  • O. A. Zagulyaeva
    • 1
  • S. F. Bychkov
    • 1
  • V. P. Mamaev
    • 1
  1. 1.Novosibirsk Institute of Organic ChemistrySiberian Branch of the Academy of Sciences of the USSRNovosibirsk

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