Reaction of 6-methyl-2-(2-oxo-2-phenyl-ethylidene)-2,3-dihydropyrimidin-4(1H)-one with hydrazine and hydroxylamine
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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.
Keywordshydrazine hydroxylamine imidazole N-oxides pyrazoles pyrimidine oximes pyrimidines pyrimidine ring transformation
This work was carried out within the joint program "Ukraine National Academy of Sciences – Russian Foundation for Basic Research" (No. 21-10).
- 1.A. V. Ivashchenko and O. N. Garicheva, Khim. Geterotsikl. Soedin., 579 (1982). [Chem. Heterocycl. Compd., 18, 429 (1982)].Google Scholar
- 2.A. A. Yavolovskii, E. I. Ivanov, and R. Yu. Ivanova, Zh. Obshch. Khim., 73, 1402 (2003).Google Scholar
- 3.A. A. Yavolovskii and E. I. Ivanov, Khim. Geterotsikl. Soedin., 443 (2004). [Chem. Heterocycl. Compd., 40, 361 (2004)].Google Scholar
- 5.D. H. Hayes and F. Hayes-Baron, J. Chem. Soc. C, 1528 (1967).Google Scholar
- 7.M. E. C. Biffin, D. J. Brown, and Q. N. Porter, J. Chem. Soc. C, 2159 (1968).Google Scholar
- 10.A. A. Yavolovskii, E. I. Ivanov, V. D. Kishichenko, and O. A. Oleinichenko, Zh. Obshch. Khim., 75, 493 (2005).Google Scholar
- 11.A. A. Yavolovskii, I. M. Rakipov, and G. L. Kamalov, Zh. Obshch. Khim., 81, 349 (2011).Google Scholar
- 13.A. Felix and P. Friedlaender, Monatsh. Chem., 31, 75 (1900).Google Scholar