Advertisement

Chemistry of Heterocyclic Compounds

, Volume 47, Issue 8, pp 989–995 | Cite as

Synthesis of alkyl hexahydropyrazino-[1,2-c]pyrimidine-9-carboxylates

  • M. V. VovkEmail author
  • O. V. Kushnir
  • N. V. Melˈnichenko
  • I. F. Tsymbal
Article

Cyclocondensation of 3-alkoxycarbonylmethylidenepiperazin-2-ones with α-chlorobenzyl isocyanates gave alkyl 8-aryl-1,6-dioxo-1,3,4,6,7,8-hexahydro-2H-pyrazino[1,2-c]pyrimidine-9-carboxylates. The use of 1-aryl-2,2,2-trifluoroethyl isocyanates in an analogous cyclization gave 6-aryl-1,8-dioxo-6-trifluoromethyl-1,3,4,6,7,8-hexahydro-2H-pyrazino[1,2-c]pyrimidine-9-carboxylates.

Keywords

3-alkoxycarbonylmethylidenepiperazin-2-ones 1-aryl-2,2,2-trifluoroethyl isocyanates α-chlorobenzyl isocyanates pyrazino[1,2-c]pyrimidine-9-carboxylates cyclocondensation. 

References

  1. 1.
    D. P. Sahu, Indian J. Chem., 37B, 1149 (1998).Google Scholar
  2. 2.
    S. Sengupta, D. P. Sahu, and S. K. Chatterjee, Liebigs Ann. Chem., 437 (1993).Google Scholar
  3. 3.
    B. Anders, K. Konrad, K. Bengt, A. Sigvard, A. Lisbeth, and S. E. H. Hernestam, Ger. Pat. Appl. 19772837089; Chem. Abstr., 90, 204134 (1979).Google Scholar
  4. 4.
    S. Herrero, A. Salgado, M. T. Garcia-Lopes, and R. Herrant, Tetrahedron Lett., 43, 4899 (2002).CrossRefGoogle Scholar
  5. 5.
    N. Anand, R. K. Chatterjee, R. N. Iyer, R. Sakena, and A. B. Sen, US Pat. Appl. 19713560503; Chem. Abstr., 74, 141845 (1979).Google Scholar
  6. 6.
    N. Anand, R. Sakena, R. K. Chatterjee, R. N. Iyer, and A. B. Sen, Brit. Pat. Appl. 19721284582; Chem. Abstr., 77, 152226 (1972).Google Scholar
  7. 7.
    S. Sharma, R. Bindra, R. N. Iyer, and N. Anand, J. Med. Chem., 18, 913 (1975).CrossRefGoogle Scholar
  8. 8.
    M. V. Vovk and V. A. Sukach, Zh. Org. Khim., 41, 1261 (2005).Google Scholar
  9. 9.
    V. A. Sukach, A. V. Bol’but, A. D. Sinitsa, and M. V. Vovk, Synlett, 375 (2006).Google Scholar
  10. 10.
    M. V. Vovk, O. V. Kushnir, V. A. Sukach, and I. F. Tsymbal, Zh. Org. Khim. 46, 716 (2010).Google Scholar
  11. 11.
    V. Y. Iwanami, Bull. Chem. Soc. Jpn., 44, 1311 (1971).CrossRefGoogle Scholar
  12. 12.
    J. Toman, J. Klichar, and V. Machacek, Collect. Czech. Chem. Commun., 43, 2179 (1978).Google Scholar
  13. 13.
    M.-J. Fan, G.-Q. Li, and Y.-M. Liang, Tetrahedron, 62, 6782 (2006).CrossRefGoogle Scholar
  14. 14.
    V. I. Gorbatenko and L. I. Samarai, Synthesis, 85 (1980)Google Scholar
  15. 15.
    L. Ambroise, D. Desmaele, and J. d'Angelo, Tetrahedron Lett., 35, 9705 (1994).CrossRefGoogle Scholar
  16. 16.
    M. V. Vovk and V. V. Pirozhenko, Khim. Geterotsikl. Soedin., 96 (1994). [Chem. Heterocycl. Comp., 30, 85 (1994)].Google Scholar
  17. 17.
    M. V. Vovk, P. S. Lebed', V. A. Sukach, and M. Yu. Kornilov, Zh. Org. Khim. , 39, 1852 (2003).Google Scholar
  18. 18.
    O. V. Kushnir, V. A. Sukach, and M. V. Vovk, Zh. Org. Khim., 45, 768 (2009).Google Scholar
  19. 19.
    V. N. Fetyukhin, A. S. Koretskii, V. I. Gorbatenko, and L. I. Samarai, Zh. Org. Khim., 13, 271 (1977).Google Scholar

Copyright information

© Springer Science+Business Media, Inc. 2011

Authors and Affiliations

  • M. V. Vovk
    • 1
    Email author
  • O. V. Kushnir
    • 2
  • N. V. Melˈnichenko
    • 1
  • I. F. Tsymbal
    • 1
  1. 1.Institute of Organic ChemistryNational Academy of Sciences of UkraineKyivUkraine
  2. 2.Yu. Fedkovich Chernivtsi National UniversityChernivtsiUkraine

Personalised recommendations