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Chemistry of Heterocyclic Compounds

, Volume 18, Issue 3, pp 300–306 | Cite as

Chemical properties of ylidene derivatives of azines. 1. Structure of the products of protonation of dihydro-2-pyrimidylidene- and dihydro-4-pyrimidylidenecyanoacetic esters

  • O. A. Zagulyaeva
  • O. A. Grigorkina
  • V. I. Mamatyuk
  • V. P. Mamaev
Article
  • 51 Downloads

Abstract

The structure of the products of protonation of dihydro-2-pyrimidylidene- and dihydro-4-pyrimidylidenecyanoacetic esters was investigated by means of IR, UV, and 1H and 13C NMR spectroscopy. It is shown that, in contrast to the corresponding α-derivative of pyridine. the investigated compounds have an ylidene structure in solutions of strong acids and in the form of perchlorates; the protons are attached to the heterocyclic nitrogen atoms.

Keywords

Nitrogen Spectroscopy Ester Organic Chemistry Pyridine 
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Literature cited

  1. 1.
    V. P. Mamaev and O. A. Zagulyaeva, Khim. Geterotsikl. Soedin., Collection 1, Nitrogen-ContainingHeterocycles, 354 (1967).Google Scholar
  2. 2.
    O. A. Zagulyaeva and V. P. Mamaev, Izv. Akad. Nauk SSSR, Ser. Khim., 2087 (1965).Google Scholar
  3. 3.
    V. V. Lapachev, O. A. Zagulyaeva, and V. P. Mamaev, Dokl. Akad. Nauk SSSR, 236, 113 (1977).Google Scholar
  4. 4.
    V. V. Lapachev, O. A. Zagulyaeva (Zagulayeva), S. F. Bichkov, and V. P. Mamaev, Tetrahedron Lett., No. 33, 3055 (1978).Google Scholar
  5. 5.
    V. V. Lapachev, O. A. Zagulyaeva, and V. P. Mamaev, Izv. Akad. Nauk SSSR, Ser. Khim., No. 11, 2633 (1977).Google Scholar
  6. 6.
    R. Wagner and W. von Philipsborn, Helv. Chim. Acta, 53, 299 (1970).Google Scholar
  7. 7.
    J. E. Douglass and J. M. Wesolosky, J. Org. Chem., 36, 1165 (1971).Google Scholar
  8. 8.
    G. V. Boyd and A. D. Ezekiel, J. Chem. Soc., C, No. 19, 1866 (1967).Google Scholar
  9. 9.
    A. Pollak, B. Stanovnik, M. Tisler, and J. Venetic-Fortunata, Monatsh. Chem., 106, 473 (1975).Google Scholar
  10. 10.
    J. Dabrowski, K. Kamienska-Trela, and L. Kozerski, Org. Magn. Reson., 6, 43 (1974).Google Scholar
  11. 11.
    H. Seel and H. Günther, J. Am. Chem. Soc., 102, 7051 (1980).Google Scholar
  12. 12.
    L. Kozerski and E. Czerwinska, Tetrahedron, 33, 1365 (1977).Google Scholar
  13. 13.
    Organic Syntheses, [in Russian], Collective Vol. 7, Inostr. Lit., Moscow (1956), p. 67.Google Scholar
  14. 14.
    G. W. Kenner, B. Lythgoe, A. R. Todd, and A. Tophan, J. Chem. Soc., No. 11, 574 (1943).Google Scholar
  15. 15.
    V. V. Lapachev, O. A. Zagulyaeva, and V. P. Mamaev, Khim. Geterotsikl. Soedin., No. 3, 395 (1977).Google Scholar

Copyright information

© Plenum Publishing Corporation 1982

Authors and Affiliations

  • O. A. Zagulyaeva
    • 1
  • O. A. Grigorkina
    • 1
  • V. I. Mamatyuk
    • 1
  • V. P. Mamaev
    • 1
  1. 1.Novosibirsk Institute of Organic Chemistry, Siberian BranchAcademy of Sciences of the USSRNovosibirsk

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