Abstract
The reaction of 4-(3-indolyl)pyrimidine methiodide with alkali gives a stable anhydro base, which reacts under mild conditions with methyl iodide to give 1-methyl-4-(1-methyl-3-indolyl)pyrimidinium iodide. On the basis of the calculated molecular diagrams of both compounds it was concluded that they have high reactivities. The reaction of the anhydro base with an aqueous methanol solution of KOH, concentrated NH4OH, hydrazine hydrate, and a mixture of malonic acid dinitrile with triethylamine leads to 3-acetylindole, 4-(3-indolyl)pyrimidine, 3(5)-(3-indolyl)pyrazole, and 2-amino-3-cyano-6-(3-indolyl)pyridine, respectively. 1-Methyl-4-(1-methyl-3-indolyl)pyrimidinium iodide under the same conditions gives similar compounds that contain a methyl group attached to the indole nitrogen atom. The structures of the synthesized compounds were confirmed by their IR, UV, PMR, and mass spectra.
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T. V. Stupnikova and Kh. Ya. Lopatinskaya, Khim. Geterotsikl. Soedin., No. 11, 1566 (1980).
E. A. Oostveen, H. C. van der Plas, and H. Iongejan, Rec. Trav. Chim., 93, 114 (1974).
R. R. Schmidt, D. Schwile, and H. Wolf, Chem. Ber., 103, 2760 (1970).
E. A. Oostveen and H. C. van der Plas, Rec. Trav. Chim., 93, 223 (1974).
A. Albert and W. Pendergast, J. Chem. Soc., Perkin Trans. I, No. 16, 1794 (1973).
A. N. Kost, R. S. Sagitullin, and G. G. Danagulyan, Khim. Geterotsikl. Soedin., No. 10, 1400 (1978).
R. S. Sagitullin and A. N. Kost, Zh. Org. Khim., 16, 658 (1980).
A. Evens and P. Caluwe, J. Org. Chem., 40, 1438 (1975).
A. K. Sheinkman, B. P. Zemskii, T. V. Stupnikova, Yu. B. Vysotskii, and A. N. Kost, Khim. Geterotsikl. Soedin., No. 11, 1477 (1978).
T. V. Stupnikova, B. P. Zemskii, Yu. B. Vysotskii, R. S. Sagitullin, and Kh. Ya. Lopatinskaya, Khim. Geterotsikl. Soedin., No. 7, 959 (1980).
B. P. Zemskii, T. V. Stupnikova, A. K. Sheinkman, and Yu. B. Vysotskii, Zh. Org. Khim., 13, 2431 (1979).
H. Biere, H. Wachtel, D. Palenschal, R. Herowski, A. Paschelke, and W. Kehr, BRD Patent No. 2406799; Ref. Zh. Khim., 120109P (1976).
A. N. Kost, L. G. Yudin, R. S. Sagitullin, and A. Muminov, Khim. Geterotsikl. Soedin., No. 11, 1566 (1978).
A. N. Kost, T. V. Stupnikova, R. S. Sagitullin, B. P. Zemskii, and A. K. Sheinkman, Dokl. Akad. Nauk SSSR, 244, 103 (1979).
T. V. Stupnikova, Kh. Ya. Lopatinskaya, B. P. Zemskii, Yu. B. Vysotskii, and R. S. Sagitullin, Khim. Geterotsikl. Soedin., No. 10, 1365 (1980).
Yu. B. Vysotskii, B. P. Zemskii, T. V. Stupnikova, R. S. Sagitullin, A. N. Kost, and O. P. Shvaika, Khim. Geterotsikl. Soedin., No. 11, 1496 (1979).
Yu. B. Vysotskii, B. P. Zemskii, T. V. Stupnikova, and R. S. Sagitullin, Khim. Geterotrsikl. Soedin., No. 3, 381 (1980).
N. A. Klyuev, T. V. Stupnikova, S. N. Baranov, and P. B. Kurapov, Dokl. Akad. Nauk Ukr SSR, Ser. B, No. 9, 47 (1980).
H. C. van der Plas and H. Iongejan, Rec. Trav. Chim., 87, 1055 (1968).
V. P. Gorbunova and N. N. Suvorov, Khim. Geterotsikl. Soedin., No. 11, 1519 (1973).
N. A. Klyuev, A. K. Sheinkman, R. A. Khmel'nitskii, G. A. Mal'tseva, and N. R. Kal'nitskii, Zh. Org. Khim., 13, 1079 (1977).
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See [1] for our preliminary communication.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 212–218, February, 1982.
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Stupnikova, T.V., Nuzhnaya, T.V., Klyuev, N.A. et al. Anhydro base of 4-(3-indolyl)pyrimidine. Chem Heterocycl Compd 18, 164–169 (1982). https://doi.org/10.1007/BF00512962
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DOI: https://doi.org/10.1007/BF00512962