REACTION OF 6-METHYL-2-(2-OXO-2-PHENYLETHYLIDENE)-2,3-DIHYDROPYRIMIDIN-4(1<i>H</i>)-ONE WITH HYDRAZINE AND HYDROXYLAMINE

Authors

  • А. А. Яволовский A. V. Bogatsky Physico-Chemical Institute, National Academy of Sciences of Ukraine
  • Л. В. Грищук A. V. Bogatsky Physico-Chemical Institute, National Academy of Sciences of Ukraine
  • И. М. Ракипов A. V. Bogatsky Physico-Chemical Institute, National Academy of Sciences of Ukraine
  • Д. Е. Степанов A. V. Bogatsky Physico-Chemical Institute, National Academy of Sciences of Ukraine
  • Ю. Э. Иванов A. V. Bogatsky Physico-Chemical Institute, National Academy of Sciences of Ukraine
  • Г. Л. Камалов A. V. Bogatsky Physico-Chemical Institute, National Academy of Sciences of Ukraine

DOI:

https://doi.org/10.1007/906

Keywords:

hydrazine, hydroxylamine, imidazole N-oxides, pyrazoles, pyrimidine oximes, pyrimidines, pyrimidine ring transformation

Abstract

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

Published

2013-08-28

Issue

Section

Original Papers