The reaction of 6-methyl-2-(2-oxo-2-phenylethylidene)-2,3-dihydropyrimidin-4(1H)-one and of its nitrosation product with hydroxylamine stops at the stage of forming the corresponding oximes. The reaction of 6-methyl-2-(2-oxo-2-phenylethylidene)-2,3-dihydropyrimidin-4(1H)-one with hydrazine yields a mixture of 3-amino-5-phenylpyrazole and 3-methyl-2-pyrazolin-5-one in 71 and 62% yields, respectively. The ketoxime is used in the synthesis of a series of imidazole N(3)-oxides substituted at the 1, 4, and 5 positions of the imidazole ring.
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This work was carried out within the joint program "Ukraine National Academy of Sciences – Russian Foundation for Basic Research" (No. 21-10).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1598–1602, October, 2012.
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Yavolovskii, A.A., Grishchuk, L.V., Rakipov, I.M. et al. Reaction of 6-methyl-2-(2-oxo-2-phenyl-ethylidene)-2,3-dihydropyrimidin-4(1H)-one with hydrazine and hydroxylamine. Chem Heterocycl Comp 48, 1487–1491 (2013). https://doi.org/10.1007/s10593-013-1162-z
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DOI: https://doi.org/10.1007/s10593-013-1162-z