Abstract
2,4,6-Trimethylpyrylium perchlorate reacts with heterocyclic compounds containing apyridine nitrogen atom and having basicities higher than 9 pKa units (in acetonitrile) through a step involving the formation of a methylenepyran. 4-Methyl-2,6-diphenyl- and 2-methyl-4,6-diphenylpyrylium perchlorates react with benzimidazole to give 1,2-ethanediylidenebispyrans. Methyl-substituted pyrylium salts react with 2,6-diphenylpyrylium and flavylium perchlorates in the presence of benzimidazole to give methylidynecyanines and with acetic anhydride to give trimethylidynecyanines.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literature cited
É. A. Zvezdina, M. P. Zhdanova, V. A. Bren', and G. N. Dorofeenko, Khim. Geterotsikl. Soedin., No. 11, 1461 (1974).
J. F. Coetzee and G. R. Padmanabhan, J. Amer. Chem. Soc., 87, 5005 (1965).
V. I. Minkin, V. A. Bren', A. D. Garnovskii, and R. I. Nikitina, Khim. Geterotsilk. Soedin., No. 4, 552 (1972).
J. A. Van Allan and G. A. Reynolds, Tetrahedron Lett., 25, 2047 (1969).
G. A. Reynolds and J. A. Van Allan, J. Heterocycl. Chem., 6, No. 5, 623 (1969).
C. C. Rentia, A. T. Balaban, and Z. Simon, Rev. Roum. Chim., 11, 1193 (1966).
G. N. Dorofeenko, E. I. Sadekova, and V. M. Goncharova, Khim. Geterotsikl. Soedin., No. 10, 1308 (1970).
J. A. Van Allan and G. A. Reynolds, J. Heterocycl. Chem., 9, No. 3, 669 (1972).
J. A. Van Allan, G. A. Reynolds, and D. P. Maier, J. Org. Chem., 33, No. 12 (1968).
Author information
Authors and Affiliations
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1484–1489, November, 1976.
Rights and permissions
About this article
Cite this article
Zvezdina, É.A., Zhdanova, M.P., Bren, V.A. et al. Reaction of methyl-substituted pyrylium salts with tertiary amines. Chem Heterocycl Compd 12, 1222–1226 (1976). https://doi.org/10.1007/BF00470218
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00470218