Abstract
It was established that the reaction of alkali with 4-(3-indolyl)pyridinium salts gives stable anhydronium bases, which are readily alkylated at the indole nitrogen atom. The pK a values of the anhydro bases were determined by spectrometry. The spectral data and reactivities are compared with the results of calculation by the self-consistent-field (SCF) MO LCAO method.
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A. R. Katritzky, Khim. Geterotsikl. Soedin., No. 8, 1011 (1972).
Yu. B. Vysotskii, N. A. Kovach, and O. P. Shvaika, Khim. Geterotsikl. Soedin., No. 9, 1186 (1977).
N. A. Klyuev, A. K. Sheinkman, R. A. Khmel'nitskii, G. A. Mal'tseva, and N. A. Kal'nitskii, Zh. Org. Khim., 13, 1079 (1977).
S. Goodwin, A. F. Smith, and E. C. Hornina, J. Am. Chem. Soc., 81, 1903 (1959).
G. T. Tatevosyan, Anhydronium Bases of the Carboline Series [in Russian], Yerevan (1966), p. 78.
V. V. S. Iyer and R. Robinson, J. Chem. Soc., 1635 (1934).
J. Bergman, J. Heterocycl. Chem., 7, 1071 (1970).
W. J. Fanshawe, V. J. Bauer, S. R. Safir, D. A. Blickens, and S. J. Riggi, J. Med. Chem., 13, 993 (1970).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1477–1481, November, 1978.
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Sheinkman, A.K., Zemskii, B.P., Stupnikova, T.V. et al. Acid-base transformations of quaternary salts of pyridylindoles. Chem Heterocycl Compd 14, 1199–1203 (1978). https://doi.org/10.1007/BF00509736
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DOI: https://doi.org/10.1007/BF00509736