Abstract
The reaction of 2,6-diphenylpyrylium perchlorate with semi- and thiosemicarbazides in ethanol leads to 1-carbamoyl- and 1-thiocarbamoyl-3-phenyl-5-phenacyl-4,5-dihydropyrazoles, the cyclization of which yields 2,5-diphenyl-7-oxo(thio)-pyrazolo[1,5-c]pyrimidines. The tautomeric form of the latter is established by comparing their electronic absorption spectra with the spectra of the methyl derivatives.
Similar content being viewed by others
Literature Cited
é. A. Zvezdina, M. P. Zhdanova, and I. I. Giryavenko, Khim. Geterotsikl. Soedin., No. 7, 893 (1983).
é. A. Zvezdina, A. N. Popova, A. I. Pyshchev, and G. N. Dorofeenko, Khim. Geterotsikl. Soedin., No. 4, 461 (1982).
é. A. Zvezdina, M. P. Zhdanova, and G. N. Dorofeenko, Khim. Geterotsikl. Soedin., No. 3, 324 (1979).
A. T. Balaban, Tetrahedron, 24, 5059 (1968).
O. Buchardt, C. L. Pedersen, U. Svanholm, A. M. Duffield, and A. T. Balaban, Acta Chem. Scand., 23, 3125 (1969).
E. Kranz, J. Kurz, and W. Donner, Chem. Ber., 105, 388 (1972).
K. Takagi and M. Hubert-Habart, Bull. Soc. Chim. France, No. 3–4, 369 (1977).
K. Kazunori, H. Masaaki, and O. Toshihiko, Chem. Pharm. Bull., 22, No. 8, 1814 (1974).
H. V. Dobeneck and A. Uhe, Annalen, No. 10, 1550 (1974).
R. Madhow, Org. Prep. Proc., 8, 200 (1976).
é. A. Zvezdina, M. P. Zhdanova, O. S. Anisimova, and G. N. Dorofeenko, Khim. Geterotsikl Soedin., No. 5, 695 (1983).
P. Molina, A. Tarraga, and C. Serrano, Tetrahedron, 40, 4901 (1984).
A. R. Katritzky and A. T. Tarraga, Heterocycles, 18, 21 (1982).
Author information
Authors and Affiliations
Additional information
For Communication 14, see [1].
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1635–1640, December, 1986.
Rights and permissions
About this article
Cite this article
Zvezdina, é.A., Zhdanova, M.P., Anisimova, O.S. et al. Reactions of heterocyclic cations with n-containing nucleophiles. 15. Reaction of 2,6-diphenylpyrylium perchlorate with semi- and thiosemicarbazides. Chem Heterocycl Compd 22, 1322–1326 (1986). https://doi.org/10.1007/BF00474352
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00474352