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Chemistry of Heterocyclic Compounds

, Volume 48, Issue 10, pp 1487–1491 | Cite as

Reaction of 6-methyl-2-(2-oxo-2-phenyl-ethylidene)-2,3-dihydropyrimidin-4(1H)-one with hydrazine and hydroxylamine

  • A. A. Yavolovskii
  • L. V. Grishchuk
  • I. M. Rakipov
  • D. E. Stepanov
  • Yu. E. Ivanov
  • G. L. Kamalov
Article

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.

Keywords

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

Notes

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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Copyright information

© Springer Science+Business Media New York 2013

Authors and Affiliations

  • A. A. Yavolovskii
    • 1
  • L. V. Grishchuk
    • 1
  • I. M. Rakipov
    • 1
  • D. E. Stepanov
    • 1
  • Yu. E. Ivanov
    • 1
  • G. L. Kamalov
    • 1
  1. 1.A. V. Bogatsky Physico-Chemical InstituteNational Academy of Sciences of UkraineOdessaUkraine

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