Abstract
The reaction of 2-(1-hydroxyimino-2-oxo-2-phenylethyl)-6-R-pyrimidin-4(3H)-ones with an excess of p-toluenesulfochloride proceeds in two stages involving consecutive oxidation of the oxygen atom of the hydroxyimino group and the oxygen atom of the amide fragment of the pyrimidine ring. The reaction of the resulting ditosylates with ethylenediamine proceeds via replacement of the sulfonyl group in the 2-position of the pyrimidine ring. The examples of 2-[1-benzoyl-2-(2-furyl)vinyl]-6-methylpyrimidin-4(3H)-one, 2-[2-(4-nitrophenyl)vinyl]-6-methylpyrimidine-4(3H)-one, and 6-methyl-2-(2-oxo-2-phenylethylthio)pyrimidin-4(3H)-one were used to consider the relationship between the structure of the substrate and the direction of the tosylation reaction.
Similar content being viewed by others
REFERENCES
Ivanov, E.I., Yavolovskii, A.A., Kuklenko, E.A., and Timofeev, O.C., Chem. Heterocycl. Compd., 1991, vol. 27, p. 225. https://doi.org/10.1007/BF00476763
Yavolovskii, A.A., Ivanov, Yu.E., Grishchuk, L.V., Kravtsov, V.Kh., Fonari, M.S., and Kamalov, G.L., Russ. J. Org. Chem., 2018, vol. 54, p. 1213. https://doi.org/10.1134/S1070428018080158
Zeifman, Yu.V., Abduganiev, E.G., Rokhlin, E.M., and Knunaynz, I.L., Russ. Chem. Bull., 1972, vol. 12, p. 2667. https://doi.org/10.1007/BF00849836
Kostyanovsky, R.G., Shustov, G.V., and Markov, V.I., Russ. Chem. Bull., 1974, vol. 23, p. 2725. https://doi.org/10.1007/BF00923717
Petukhova, V.Yu., Strelenko, Yu.A., Lyssenko, K.A., and Makhova, N.N., Russ. Chem. Bull., 2007, vol. 56, p. 1550. https://doi.org/10.1007/s11172-007-0241-7
Vedres, A., Szantay, Cs., Balogh, Gy., Horvath, J., and Mester, T., FI Patent Appl. no. FI793307 (A), 1980.
Martirosyan, Z.A., Gunar, V.I., and Zav’yalov, S.I., Russ. Chem. Bull., 1970, vol. 19, p. 1732. https://doi.org/10.1007/BF00996514
Kaznar, B., Krizmanic, I., and Zinic, M., Nucleosides Nucleotides, 1997, vol. 16, p. 1067. https://doi.org/10.1080/07328319708006134
Janeba, Z., Balzarini, J., Graciela, A., Snoeck, R., De Clercq, E., and Robins, M.J., Can. J. Chem., 2006, vol. 84, p. 580–586. https://doi.org/10.1139/V06-041
Yavolovskii, A.A., Grishchuk, L.V., Rakipov, I.M., Stepanov, D.E., Ivanov, Yu.E., and Kamalov, G.L., Chem. Heterocycl. Compd., 2013, vol. 10, p. 1487. https://doi.org/10.1007/s10593-013-1162-z
Yavolovskii, A.A., Grishchuk, L.V., Bevzyuk, E.I., Pluzhnik-Gladyr, S.M., and Kamalov, G.L., Russ. J. Gen. Chem., 2014, vol. 84, p. 869. https://doi.org/10.1134/S1070363214050156
Hurst, D.T., Beautont, C., Jones, D.T.E., Kingsley, D.A., Partridge, J.D., and Rutherford, T.J., Aust. J. Chem., 1988, vol. 41, p. 1209. https://doi.org/10.1071/CH9881209
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
The authors declare no conflict of interest.
Additional information
Translated from Zhurnal Organicheskoi Khimii, 2021, Vol. 57, No. 11, pp. 1599–1605 https://doi.org/10.31857/S0514749221110057.
Rights and permissions
About this article
Cite this article
Yavolovskii, A.A., Stepanov, D.E., Grishchuk, L.V. et al. Specific Features of Tosylation of 2-Substituted Pyrimidin-4(3H)-ones Containing a Double Bond in the α-Position of the Side Chain. Russ J Org Chem 57, 1841–1846 (2021). https://doi.org/10.1134/S1070428021110051
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070428021110051