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
O. P. Petrenko and V. V. Lapachev, Zh. Org. Khim. (in press).
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).
N. S. Zefirov and S. S. Trach, Zh. Org. Khim., 12, 697 (1976).
B. Pilarsky, H. Foks, K. Osmialowski, and R. Kaliszan, Monatsh. Chem., 115, 179 (1984).
S. K. Chakrabartty and R. Levine, J. Heterocycl. Chem., 4, 109 (1967).
R. Mondelly and L. Merlini, Tetrahedron, 22, 3253 (1966).
J. S. England and J. C. Guyon, Microchim. Acta, No. 6, 935 (1973).
M. I. Kabachnik, Zh. Vsesoyuzn. Khim. Obshchestva, 7, 263 (1962).
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).
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.
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.
S. A. Stekhova, V. V. Lapachev, and V. P. Mamaev, Khim. Geterotsikl. Soedin., No. 7, 994 (1981).
J. D. Behun and R. Levine, J. Am. Chem. Soc., 81, 5157 (1959).
J. F. Wolfe, D. E. Portlock, and D. J. Feuerbach, J. Org. Chem., 39, 2006 (1974).
E. H. Sund and D. L. Callender, J. Chem. Eng. Data, 25, 189 (1980).
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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