Skip to main content
Log in

Synthesis of 6-methyl-2-[2-phenyl-2-(arylhydrazono)ethyl]-3Н-pyrimidine-4-ones and their oxidation by hydrogen peroxide and selenium dioxide

  • Published:
Russian Journal of General Chemistry Aims and scope Submit manuscript

Abstract

The reaction of 6-methyl-2-(2-oxo-2-phenylethylidene)-2,3-dihydropyrimidine-4(1H)-one with arylhydrazines leads in high yields to the corresponding hydrazones, in which the ethylidene fragment of the starting compound is transformed to the ethylene fragment. By oxidation of the hydrazones with hydrogen peroxide or selenium dioxide the corresponding 6-methyl-2-[2-phenyl-2-(arylhydrazono)acetyl]-3H-pyrimidine-4-ones were synthesized.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Iffland, D.S., Salisbery, L., and Schafer, W.R., J. Am. Chem. Soc., 1961, vol. 83, p. 747. DOI: 10.1021/ja01464a049.

    Article  CAS  Google Scholar 

  2. Buckingham, J., Quart. Rev., 1969, vol. 23, p. 37. DOI: 10.1039/QR9692300037.

    Article  CAS  Google Scholar 

  3. Karnozhitskii, V., Russ. Chem. Rev., 1977, vol. 46, no. 2, p. 121. DOI: 10.1070/RC1977v046n02ABEH002123.

    Article  Google Scholar 

  4. Chernova, A.V., Shagidullin, R.R., and Kitaev, Yu.P., Zh. Org. Khim., 1967, vol. 3, no. 5, p. 916.

    CAS  Google Scholar 

  5. Ito, Y., Kyono, K., and Matsuuro, T., Tetrahedron Lett., 1979, no. 24, p. 2253. DOI: 10.1016/S0040-4039(01) 93690-1.

    Article  Google Scholar 

  6. Vevien, F. and Mandrier, C., C. R. Acad. Sc. Paris. Ser. C, 1970, vol. 270, p. 845.

    Google Scholar 

  7. Yavolovskii, A.A., Ivanov, E.I., and Ivanova, R.Yu., Russ. J. Gen. Chem., 2003, vol. 73, no. 8, p. 1326. DOI: 10.1023/B:RUGC.0000007670.73042.92.

    Article  CAS  Google Scholar 

  8. Yavolovskii, A.A. and Ivanov, E.I., Chem. Heterocycl. Compd., 2004, vol. 40, no. 3, p. 361. DOI: 10.1023/B:COHC.0000028633.76885.60.

    Article  CAS  Google Scholar 

  9. Simonov, Y.A., Fonari, M.S., Lipkowski, J., Yavolovskii, A.A., and Ganin, E.V., J. Inclusion Phenomena. Macrocycl. Chem., 2003, vol. 46, nos. 1–2, p. 27. DOI: 10.1023/A:1025612912040.

    Article  CAS  Google Scholar 

  10. Yavolovskii, A.A., Kishichenko, V.D., Oliinichenko, O.A., and Ivanov, E.I., Russ. J. Gen. Chem., 2005, vol. 75, no. 3, p. 457. DOI: 10.1007/s11176-005-0249-3.

    Article  CAS  Google Scholar 

  11. Yavolovskii, A.A., Rakipov, I.M., and Kamalov, G.L., Russ. J. Gen. Chem., 2011, vol. 81, no. 2, p. 447. DOI: 10.1134/S1070363211020356.

    Article  CAS  Google Scholar 

  12. Yavolovskii, A.A., Grishchuk, L.V., Rakipov, I.M., Stepanov, D.E., Ivanov, Yu.E., and Kamalov, G.L., Chem. Heterocycl. Compd., 2013, vol. 48, no. 10, p. 1487. DOI: 10.1007/s10593-013-1162-z.

    Article  CAS  Google Scholar 

  13. Harst, D.T., Beaumont, C., Jones, D.T.E., Kingsley, D.A., Partridge, J.D., and Rutherford, T.J., Austr. J. Chem., 1988, vol. 41, p. 1209. DOI: 10.1071/CH9881209.

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to S. M. Pluzhnik-Gladyr.

Additional information

Original Russian Text © A.A. Yavolovskii, S.M. Pluzhnik-Gladyr, Yu.E. Ivanov, D.E. Stepanov, L.V. Grishchuk, G.L. Kamalov, 2016, published in Zhurnal Obshchei Khimii, 2016, Vol. 86, No. 7, pp. 1126–1129.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Yavolovskii, A.A., Pluzhnik-Gladyr, S.M., Ivanov, Y.E. et al. Synthesis of 6-methyl-2-[2-phenyl-2-(arylhydrazono)ethyl]-3Н-pyrimidine-4-ones and their oxidation by hydrogen peroxide and selenium dioxide. Russ J Gen Chem 86, 1604–1607 (2016). https://doi.org/10.1134/S1070363216070112

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363216070112

Keywords

Navigation