Abstract
It is shown that contraction of the pyrimidine ring occurs when 6-nitro-7-oxo-4,7-dihydroazolo[1,5-a]pyrimidines are heated with hydrazine hydrate. Complexes of 4-nitropyrazole with 5-aminoazoles, the structures of which were proved by x-ray diffraction analysis, are formed in a similar reaction of nitrosubstituted azolopyrimidines that do not contain an oxo function.
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Literature Cited
V. L. Rusinov, A. A. Tumashov, T. L. Pilicheva, and O. N. Chupakhin, Zh. Org. Khim. (in press).
M. E. C. Biffin, D. J. Brown, and Q. N. Porter, Tetrahedron Lett., No. 21, 2029 (1967).
S. Senda, K. Hirota, T. Asao, and Y. Ymoda, Heterocycles, 4, 1765 (1976).
J. Clark and M. Curphey, J. Chem. Soc., No. 5, 184 (1974).
V. L. Rusinov, T. L. Pilicheva, A. A. Tumashov, and O. N. Chupakhin, Khim. Geterotsikl. Soedin., No. 6, 357 (1987).
O. N. Chupakhin, V. L. Rusinov, A. A. Tumashov, T. L. Pilicheva, E. O. Sidorov, and I. V. Karpin, Khim. Geterotsikl. Soedin., No. 2, 256 (1991).
J. L. Barascut, R. M. Claramuni, and J. Elguero, Bull. Soc. Chim. France, No. 5, 1849 (1973).
V. L. Rusinov, I. Ya. Postovskii, A. Yu. Petrov, E. O. Sidorov, and Yu. A. Azev, Khim. Geterotsikl. Soedin., No. 11, 1554 (1981).
V. L. Rusinov, A. Yu. Petrov, T. L. Pilicheva, O. N. Chupakhin, G. V. Kovelev, and E. R. Komina, Khim.-farm. Zh., No. 2, 178 (1986).
K. Schofild, M. R. Crimmett, and B. R. T. Keene, The Azoles, Cambridge University Press, Cambridge (1976), p. 318.
E. Alcalde, J. Mendoza, J. M. Garcia-Marguina, C. Almera, and J. Elguero, J. Heterocycl. Chem., 11, 423 (1974).
I. I. Grandberg, Din Vei-py, and A. N. Kost, Zh. Obshch. Khim., 31, 2311 (1961).
M. M. Williams, S. E. William, and R. A. Henry, J. Phys. Chem., 61, 261 (1957).
G. T. Morgan and J. Reilly, J. Chem. Soc., 109, 155 (1916).
V. A. Lopyrev, L. P. Sidorova, O. A. Netsetskaya, and M. P. Grindblat, Zh. Obshch. Khim., No. 11, 2525 (1969).
J. N. Vishwakarma and Chowdhury, Indian J. Chem., 824, 472 (1985).
J. L. Barascut, P. Viallefont, and J. Daunis, Bull. Soc. Chim. France, Nos. 7–8, 1648 (1975).
R. Hoftel, F. Buchebe, and P. Jochum, Chem. Ber., 88, 1577 (1955).
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See [1] for Communication 14.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 665–668, May, 1991.
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Rusinov, V.L., Myasnikov, A.V., Chupakhin, O.N. et al. Nitroazines. 15. Contraction of the pyrimidine ring in 6-nitroazolo[1,5-a]pyrimidines. Chem Heterocycl Compd 27, 530–533 (1991). https://doi.org/10.1007/BF00474001
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DOI: https://doi.org/10.1007/BF00474001