Chemistry of Heterocyclic Compounds

, Volume 16, Issue 6, pp 640–644 | Cite as

Tautomerism of azine derivatives. 4. Keto-enol tautomerism of β-keto esters of the azine series

  • S. A. Stekhova
  • O. A. Zagulyaeva
  • V. V. Lapachev
  • V. P. Mamaeva


The structures of pyrazinoyl-, 3-pyridazinoyl-, 4-pyrimidoyl-, and 2-, 3-, and 4-pyridoylacetic esters were studied by means of IR, NMR, and1H and13C NMR spectroscopy and quantum-chemical calculations (Pariser-Parr-Pople and CNDO/2). The effect of solvents (including strongly and weakly basic solvents) on the position of the tautomeric equilibria of these β-keto esters was studied. The o+ constants for the keto and enol fragments were estimated by means of quantum-chemical calculations and13C NMR spectroscopy.


Spectroscopy Ester Organic Chemistry Enol Azine 
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Literature cited

  1. 1.
    V. V. Lapachev, O. A. Zagulyaeva, S. S. Bychkòv, and V. P. Mamaev, Khim. Geterotsikl. Soedin., No. 12, 1544 (1978).Google Scholar
  2. 2.
    V. V. Lapachev, O. A. Zagulyaeva, and V. P. Mamaev, Khim. Geterotsikl. Soedin., No. 8, 1136 (1975).Google Scholar
  3. 3.
    G. Henich, Monatsh.,104, 953.Google Scholar
  4. 4.
    N. S. Prostakov, A. Ya. Ismailov, V. P. Zvolinskii, and D. A. Fesenko, Khim. Geterotsikl. Soedin., No. 2, 230 (1973).Google Scholar
  5. 5.
    A. I. Kol'tsov and G. M. Kheifets, Usp. Khim.,40, 1646 (1971).Google Scholar
  6. 6.
    N. S. Golubev, G. S. Denisov, and A. I. Kol'tsov, Dokl. Akad. Nauk SSSR,230, 880 (1976).Google Scholar
  7. 7.
    M. Konde, Bull. Chem. Soc. Jpn.,52, 521 (1979).Google Scholar
  8. 8.
    L. Bellamy, Infrared Spectra of Complex Molecules, Methuen, London (1958).Google Scholar
  9. 9.
    I. A. Grigor'ev, G. I. Shchukin, and L. B. Volodarskii, Izv. Sibirsk. Otd. Akad. Nauk SSSR, No. 9, 135 (1977).Google Scholar
  10. 10.
    F. Rossotti and H. Rossotti, J. Chem. Soc., 1304 (1958).Google Scholar
  11. 11.
    D. Kh. Zheglova, B. A. Ershov, and A. I. Kol'tsov, Zh. Org. Khim.,10, 18 (1974).Google Scholar
  12. 12.
    R. Gelin, S. Gelin, and M. Zambartas, C. R., C,270, 832 (1970).Google Scholar
  13. 13.
    J. Niwa, M. Yamazaki, and T. Takeuchi, Chem. Lett., 707 (1975).Google Scholar
  14. 14.
    V. V. Lapachov, S. F. Bichkov, O. A. Zagulyaeva, and V. P. Mamaev, Tetrahedron Lett., 3055 (1978).Google Scholar
  15. 15.
    D. Kh. Zheglova, Yu. M. Boyarchuk, B. A. Ershov, and A. I. Kol'tsov, Zh. Org. Khim.,11, 2400 (1974).Google Scholar
  16. 16.
    L. Hammett, Fundamentals of Physical Organic Chemistry [Russian translation], Mir, Moscow (1972), p. 14.Google Scholar
  17. 17.
    G. L. Nelson and G. C. Levy, J. Am. Chem. Soc.,94, 3089 (1972).Google Scholar
  18. 18.
    W. H. de Jen, J. Phys. Chem.,74, 822 (1970).Google Scholar
  19. 19.
    G. Karlström, J. Am. Chem. Soc., 97, 4188 (1975).Google Scholar
  20. 20.
    Table of Interatomic distances and Configurations in Molecules and Ions, Chem. Soc., London (1958); Supplement (1963).Google Scholar
  21. 21.
    J. C. Godfrey, in: Pyridine and Its Derivatives, Part 3, New York-London (1964), pp. 388, 389, 390.Google Scholar
  22. 22.
    S. A. Hall and E. Spoerri, J. Am. Chem. Soc.,62, 664 (1940).Google Scholar
  23. 23.
    W. J. Leanza, H. J. Becker, and E. F. Rogers, J. Am. Chem. Soc.,75, 4086 (1953).Google Scholar
  24. 24.
    J. Wong, M. Brown, and H. Rapoport, J. Org. Chem.,30, 2398 (1965).Google Scholar

Copyright information

© Plenum Publishing Corporation 1980

Authors and Affiliations

  • S. A. Stekhova
    • 1
  • O. A. Zagulyaeva
    • 1
  • V. V. Lapachev
    • 1
  • V. P. Mamaeva
    • 1
  1. 1.Novosibirsk Institute of Organic Chemistry, Siberian BranchAcademy of Sciences of the USSRNovosibirsk

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