Abstract
By reaction of 4-substituted 5-amino-6-mercaptopyrimidines with 5-bromo-2,2-dimethyl-4,6-dioxo-1,3-dioxane, we have obtained 4′-substituted 5-(5-amino-6-pyrimidylthio)-2,2-dimethyl-4,6-dioxo-1,3-dioxanes. We have studied diazotization of these compounds by isoamyl nitrite. In the case of 4′-methoxy- and 4′-dimethylamino-substituted derivatives, we have obtained derivatives of novel heterocyclic systems: pyrimido[5,4-e][1,3,4]thiadiazine and pyrimido[5,4-e][1,3,4]thiadiazine-7-spiro-5′-1,3-dioxane, and in the case of the 4′-isopropylamino-substituted derivative we obtained 4-isopropyl-7-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)-1,2,3-triazolo[5,4-d]pyrimidin-7-ylidene.
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REFERENCES
T. S. Safonova, M. P. Nemeryuk, M. M. Likhovidova, A. L. Sedov, N. A. Grineva, M. A. Keremov, N. P. Solov’eva, O. S. Anisimova, and A. S. Sokolova, Khim.-Farm. Zh., 37, No.6, 21 (2003).
M. P. Nemeryuk, O. L. Mushnikova, E. M. Peresleni, T. F. Vlasova, I. V. Persianova, Yu. N. Sheinker, and T. S. Safonova, Khim. Geterotsikl. Soedin., 755 (1980)
M. P. Nemeryuk, O. L. Mushnikova, M. V. Pykhova, A. F. Keremov, N. A. Ryabokon’, Yu. A. Ershova, A. S. Sokolova, V. A. Chernov, and T. S. Safonova, Khim.-Farm. Zh., 13, No.8, 51 (1979).
M. Eigen, G. Ilgenfritz, and W. Kruse, Chem. Ber., 98, 1623 (1965).
H. McNab, Chem. Soc. Rev., 7, 345 (1978).
M. P. Nemerjuk, A. L. Sedov, T. S. Safonova, A. Cerny, and J. Krepelka, Coll. Czech., 51, 215 (1986).
K. V. Vatsuro and G. A. Mishchenko, Name Reactions in Organic Chemistry [in Russian], Khimiya, Moscow (1976), p. 509.
M. Iehida and K. Senga, J. Heterocycl. Chem., 22, 381 (1985).
A. J. Elliott, US Patent 4025510; Chem. Abstr. 153420 (1977).
W. D. Pfeiffer, E. Dilk, and E. Bulka, Z. Chem., No. 6, 218 (1977).
M. P. Nemeryuk and T. S. Safonova, Khim. Geterotsikl. Soedin., 192 (1975).
E. S. Taylor, J. W. Barton, and W. W. Paudler, J. Org. Chem., 26, 4961 (1961).
J. Clark, I. Gelling, I. W. Southon, and M. S. Morton, J. Chem. Soc. (C), 494 (1970).
M. P. Nemeryuk, A. L. Sedov, J. Krepelka, and T. S. Safonova, Khim. Geterotsikl. Soedin., 1426 (1982).
H. R. Snyder and C. W. Kruse, J. Am. Chem. Soc., 80, 1942 (1958).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 613–623, April, 2005.
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Safonova, T.S., Nemeryuk, M.P., Likhovidova, M.M. et al. Study of Nitrogen- and Sulfur-Containing Heterocycles. 57. Synthesis and Conversion of 4′-Substituted 5-(5-Amino-6-Pyrimidylthio)-2,2-Dimethyl-4,6-Dioxo-1,3-Dioxanes. Chem Heterocycl Compd 41, 526–535 (2005). https://doi.org/10.1007/s10593-005-0182-8
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DOI: https://doi.org/10.1007/s10593-005-0182-8