Abstract
Recyclization of 2-(2-acylethyl)pyridinium salts on treatment with nucleophiles may occur in different ways, to give heterocyclic compounds of various classes, namely indoles (the Kost-Sagitullin reaction products), 4-aminoindoles, and 3-hydroxy-1,2,3,4-tetrahydroquinolines, the formation of which constitute novel reactions in the recyclization of pyridinium salts.
Similar content being viewed by others
Literature Cited
P. B. Terent'ev, Lieh Ty Chin, and A. N. Kost, Khim. Geterotsikl. Soedin., No. 6, 800 (1981).
R. S. Sagitullin, S. N. Gromov, and A. N. Kost, Dokl. Akad. Nauk SSSR, 234, 121 (1978).
H. Albrecht and F. Krohnke, Tetrahedron Lett., No. 11, 967 (1967).
A. N. Kost, R. S. Sagitullin, and S. P. Gromov, Dokl. Akad. Nauk SSSR, 230, 1106 (1976).
M. A. Yurovskaya, V. A. Chertkov, A. Z. Afanas'ev, F. V. Ienkina, and Yu. G. Bundel', Khim. Geterotsikl. Soedin., No. 4, 509 (1985).
V. Boekelheide, W. Y. Linn, P. O'Grady, and M. Lambord, J. Am. Chem. Soc., 75, 3243 (1953).
G. Cainelli, M. Panunzio, and A. Umani-Ronchi, J. Chem. Soc., Perkin I, No. 13, 1273 (1975).
H. M. Kissman, D. W. Farnsworth, and B. Witkop, J. Am. Chem. Soc., 74, 3948 (1952).
Beilstein, XX(3), p. 4061.
Author information
Authors and Affiliations
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1217–1225, September, 1990.
Rights and permissions
About this article
Cite this article
Terenin, V.I., Rumyantsev, A.N., Nosyrev, P.V. et al. Recyclization of 2-(2-acylethyl)pyridinium salts. Chem Heterocycl Compd 26, 1016–1022 (1990). https://doi.org/10.1007/BF00472484
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00472484