Advertisement

Chemistry of Heterocyclic Compounds

, Volume 42, Issue 6, pp 788–791 | Cite as

Transformations of methyl 6-methyl-2-methylsulfanyl-4-oxo-3,4-dihydro-3-pyrimidinylacetate under oxidative conditions

  • V. Jakubkiene
  • P. Vainilavicius
Article

Abstract

The oxidation of methyl 6-methyl-2-methylsulfanyl-4-oxo-3,4-dihydro-3-pyrimidinylacetate by reagents which oxidized the SMe group to SO2Me gave the products of the further transformation of the corresponding 2-methylsulfonyl-substituted ester obtained: methyl 5,5-dichloro-6-methoxy-6-methyl-2,4-dioxohexahydro-3-pyrimidinylacetate (using Cl2 in 70 or 50% MeOH), its mixture (about 1:10) with methyl 6-methyl-2,4-dioxo-1,2,3,4-tetrahydro-3-pyrimidinylacetate (Cl2 in 30% MeOH) or only to the latter compound (Cl2 in H2O, m-ClC6H4CO3H in CHCl3, H2O2 in MeOH). The reaction did not take place with NaOCl in DMF.

Keywords

methyl 6-methyl-2-methylsulfanyl-4-oxo-3,4-dihydro-3-pyrimidinylacetate methyl 5,5-dichloro-6-methoxy-6-methyl-2,4-dioxohexahydro-3-pyrimidinylacetate methyl 6-methyl-2,4-dioxo-1,2,3,4-tetrahydro-3-pyrimidinylacetate 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    D. J. Brown and P. W. Ford, J. Chem. Soc., 568 (1967).Google Scholar
  2. 2.
    Z. Budesinsky and J. Vavrina, Collect. Czech. Chem. Commun., 37, 1721 (1972).Google Scholar
  3. 3.
    D.-K. Kim, J. Gam, Y.-W. Kim, J. Lim, H.-T. Kim, and K. H. Kim, J. Med. Chem., 40, 2363 (1997).CrossRefGoogle Scholar
  4. 4.
    Y. M. Volovenko and E. V. Blyumin, Tetrahedron, 56, 5185 (2000).CrossRefGoogle Scholar
  5. 5.
    A. Herrera, R. Martinez-Alvarez, R. Chioua, F. Benabdelouahab, and M. Chioua, Tetrahedron, 60, 5475 (2004).CrossRefGoogle Scholar
  6. 6.
    V. Jakubkiene, M. M. Burbuliene, G. Mekuskiene, E. Udrenaite, P. Gaidelis, and P. Vainilavicius, Farmaco, 58, 323 (2003).CrossRefGoogle Scholar
  7. 7.
    M. A. Mikhaleva, G. A. Kolesnichenko, K. I. Rubina, Yu. Sh. Gol’dberg, V. A. Savel’ev, L. Ya. Leitis, M. V. Shimanskaya, and V. P. Mamaev, Khim. Geterotsikl. Soedin., 380 (1986).Google Scholar
  8. 8.
    A. Novacek and I. Hedrlin, Collect. Czech. Chem. Commun., 32, 1045 (1967).Google Scholar
  9. 9.
    P. Vainilavichius, V. Syadyaryavichiute, and S. Mocishkite, Khim. Geterotsikl. Soedin., 1655 (1992).Google Scholar
  10. 10.
    P. I. Vainilavichyus and V. Yu. Syadyaryavichyute, Khim. Geterotsikl. Soedin., 1520 (1987).Google Scholar
  11. 11.
    T. B. Johnson and J. M. Spraque, J. Amer. Chem. Soc., 60, 1622 (1938).CrossRefGoogle Scholar
  12. 12.
    S. Y. Wang, J. Org. Chem., 24, 11 (1959).CrossRefGoogle Scholar
  13. 13.
    J. Moravek and L. Leseticky, Collect. Czech. Chem. Commun., 33, 1352 (1968).Google Scholar
  14. 14.
    P. I. Vainilavichyus and V. Yu. Syadyaryavichyute, Khim. Geterotsikl. Soedin., 1655 (1987).Google Scholar

Copyright information

© Springer Science+Business Media, Inc. 2006

Authors and Affiliations

  • V. Jakubkiene
    • 1
  • P. Vainilavicius
    • 1
  1. 1.Vilnius UniversityVilniusLithuania

Personalised recommendations