Abstract
Reaction of 6-nitroazolo[1,5-a]pyrimidines with cyanoacetamide, cyanoacetthioamide, or benzoylacetonitrile results in the conversion of the pyrimidine ring into a pyridine ring with the formation of 2-azolylamino-5-nitropyridines. Treatment of the latter with alcoholic sodium carbonate, or reaction of the azolopyrimidines with acetonitriles in an alkaline medium, affords 7-nitroazolo]1,5-a]pyrido[2,3-d]pyrimidines.
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Literature Cited
V. L. Rusinov, T. L. Pilicheva, A. A. Tumashov, G. G. Aleksandrov, E. O. Sidorov, I. V. Karpin, and O. N. Chupakhin, Khim. Geterotsikl. Soedin., No. 12, 1679 (1990).
H. C. van der Plas and J. W. Street, Aromatic and Heteroaromatic Chemistry, Vol. 4 (1976), p. 146.
V. N. Charushin and H. S. van der Plas, Rec. Trav. Chem., 108, 373 (1983).
E. Kretzchmar, Pharmazie, 35, 253 (1980).
J. M. Domalga, L. D. Hanna, C. L. Heifetz, M. P. Hutt, C. L. Sauchez, and M. Solomon, J. Med. Chem., 29, 394 (1968).
N. Suzuki, Chem. Pharm. Bull., 28, 761 (1980).
V. L. Rusinov, I. Ya. Postovskii, A. Yu. Petrov, E. O. Sidorov, and Yu. A. Azev, Khim. Geterotsikl. Soedin., No. 11, 1554 (1981).
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See [1] for communication 11.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 256–291, February, 1991.
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Chupakhin, O.N., Rusinov, V.L., Tumashov, A.A. et al. Nitroazines. 12 Reaction of 6-nitroazolo[1,5-a]pyrimidines with acetonitriles. Chem Heterocycl Compd 27, 210–215 (1991). https://doi.org/10.1007/BF00476759
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DOI: https://doi.org/10.1007/BF00476759