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Tautomerism of derivatives of azines. 16. Tautomerism of acylmethylpyrazines and -quinoxalines

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Abstract

The tautomeric equilibria of acylmethylpyrazines and -quinoxalines in chloroform were studied by 1H, 14N, and 17O NMR spectroscopy. It was shown that keto-enol tautomerism is realized in the acylmethylpyrazine series. Annelation leads to the development of an ylidene tautomer in the acylmethylquinoxaline series. A marked dependence of the position of the intrachelate equilibrium on the character of the solvent was observed.

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Literature Cited

  1. O. P. Petrenko and V. V. Lapachev, Zh. Org. Khim. (in press).

  2. V. V. Lapachev, S. A. Stekhova, I. Ya, Mainagashev, M. A. Fedotov, V. E. Hall, and V. P. Mamaev, Khim. Geterotsikl. Soedin., No. 6, 802 (1986).

    Google Scholar 

  3. N. S. Zefirov and S. S. Trach, Zh. Org. Khim., 12, 697 (1976).

    Google Scholar 

  4. B. Pilarsky, H. Foks, K. Osmialowski, and R. Kaliszan, Monatsh. Chem., 115, 179 (1984).

    Google Scholar 

  5. S. K. Chakrabartty and R. Levine, J. Heterocycl. Chem., 4, 109 (1967).

    Google Scholar 

  6. R. Mondelly and L. Merlini, Tetrahedron, 22, 3253 (1966).

    Google Scholar 

  7. J. S. England and J. C. Guyon, Microchim. Acta, No. 6, 935 (1973).

    Google Scholar 

  8. M. I. Kabachnik, Zh. Vsesoyuzn. Khim. Obshchestva, 7, 263 (1962).

    Google Scholar 

  9. V. V. Lapachev, I. Ya. Mainagashev, S. A. Stekhova, M. A. Fedotov, V. P. Krivopalov, and V. P. Mamaev, Chem. Commun., No. 8, 494 (1985).

    Google Scholar 

  10. V. P. Mamaev and V. V. Lapachev, in: Soviet Scientific Reviews, Section B, Vol. 7, edited by N. K. Kochetkov and M. E. Vol'pin, Harwood Acad. Publ., New York-London (1985), p. 1.

    Google Scholar 

  11. S. A. Stekhova, V. V. Lapachev, O. P. Petrenko, and V. P. Mamaev, in: The IX International Congress of Heterocyclic Chemistry. Abstracts, edited by T. Kametani, Hoshi University, Tokyo (1983), p. 423.

    Google Scholar 

  12. S. A. Stekhova, V. V. Lapachev, and V. P. Mamaev, Khim. Geterotsikl. Soedin., No. 7, 994 (1981).

    Google Scholar 

  13. J. D. Behun and R. Levine, J. Am. Chem. Soc., 81, 5157 (1959).

    Google Scholar 

  14. J. F. Wolfe, D. E. Portlock, and D. J. Feuerbach, J. Org. Chem., 39, 2006 (1974).

    Google Scholar 

  15. E. H. Sund and D. L. Callender, J. Chem. Eng. Data, 25, 189 (1980).

    Google Scholar 

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See [1] for Communication 15.

Deceased.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1663–1667, December, 1987.

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Mainagashev, I.Y., Lapachev, V.V., Fedotov, M.A. et al. Tautomerism of derivatives of azines. 16. Tautomerism of acylmethylpyrazines and -quinoxalines. Chem Heterocycl Compd 23, 1339–1342 (1987). https://doi.org/10.1007/BF00472261

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  • DOI: https://doi.org/10.1007/BF00472261

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