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.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
A. V. Ivashchenko and O. N. Garicheva, Khim. Geterotsikl. Soedin., 579 (1982). [Chem. Heterocycl. Compd., 18, 429 (1982)].
A. A. Yavolovskii, E. I. Ivanov, and R. Yu. Ivanova, Zh. Obshch. Khim., 73, 1402 (2003).
A. A. Yavolovskii and E. I. Ivanov, Khim. Geterotsikl. Soedin., 443 (2004). [Chem. Heterocycl. Compd., 40, 361 (2004)].
F. Lingens and H. Schneider-Bernlohr, Justus Liebigs Ann. Chem., 686, 134 (1965).
D. H. Hayes and F. Hayes-Baron, J. Chem. Soc. C, 1528 (1967).
M. E. C. Biffin, D. J. Brown, and Q. N. Porter, Tetrahedron Lett., 8, 2029 (1967).
M. E. C. Biffin, D. J. Brown, and Q. N. Porter, J. Chem. Soc. C, 2159 (1968).
K. Hirota, Y. Kitade, K. Shimada, and S. Senda, Chem. Pharm. Bull., 29, 3760 (1981).
Y. A. Simonov, M. S. Fonari, J. Lipkowski, A. A. Yavolovskii, and E. V. Ganin, J. Inclusion Phenom. Macrocyclic Chem., 46, 27 (2003).
A. A. Yavolovskii, E. I. Ivanov, V. D. Kishichenko, and O. A. Oleinichenko, Zh. Obshch. Khim., 75, 493 (2005).
A. A. Yavolovskii, I. M. Rakipov, and G. L. Kamalov, Zh. Obshch. Khim., 81, 349 (2011).
G. Ege and H. Franz, J. Heterocycl. Chem., 19, 1267 (1982).
A. Felix and P. Friedlaender, Monatsh. Chem., 31, 75 (1900).
J.-C. Jung, E. B. Watkins, and M. A. Avery, Tetrahedron, 58, 3639 (2002).
M. Jasinski, G. Mloston, A. Linden, and H. Heimgartner, Helv. Chim. Acta, 91, 1916 (2008).
D. T. Hurst, C. Beaumont, D. T. E. Jones, D. A. Kingsley, J. D. Patridge, and T. J. Rutherford, Aust. J. Chem., 41, 1209 (1988).
This work was carried out within the joint program "Ukraine National Academy of Sciences – Russian Foundation for Basic Research" (No. 21-10).
Author information
Authors and Affiliations
Corresponding author
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1598–1602, October, 2012.
Rights and permissions
About this article
Cite this article
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
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10593-013-1162-z