REACTION OF 6-METHYL-2-(2-OXO-2-PHENYLETHYLIDENE)-2,3-DIHYDROPYRIMIDIN-4(1<i>H</i>)-ONE WITH HYDRAZINE AND HYDROXYLAMINE
DOI:
https://doi.org/10.1007/906Keywords:
hydrazine, hydroxylamine, imidazole N-oxides, pyrazoles, pyrimidine oximes, pyrimidines, pyrimidine ring transformationAbstract
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.
Authors: A. A. Yavolovskii, L. V. Grishchuk, I. M. Rakipov, D. E. Stepanov, Yu. E. Ivanov, and G. L. Kamalov
English Translation in Chemistry of Heterocyclic Compounds, 2013, 48 (10), pp 1487-1491
http://link.springer.com/article/10.1007/s10593-013-1162-z