Russian Journal of Organic Chemistry

, Volume 45, Issue 6, pp 921–927 | Cite as

Synthesis of new polyfunctional 5,6,7,8-tetrahydroimidazo-[1,5-c]pyrimidin-5-ones by the aza-Wittig reaction followed by intramolecular cyclization and 1,3-prototropic shift

  • P. S. Lebed’
  • P. O. Kos
  • V. V. Polovinko
  • A. A. Tolmachev
  • M. V. Vovk


Ethyl 2-oxo-6-[(triphenyl-λ5-phosphanylidene)aminomethyl]-1,2,3,4-tetrahydropyrimidine-5-carboxylates reacted with organic isocyanates according to the aza-Wittig pattern, and the subsequent intramolecular ring closure and 1,3-H shift resulted in the formation of ethyl 3-alkyl(aryl)amino-5-oxo-5,6,7,8-tetrahydroimidazo[1,5-c]pyrimidine-8-carboxylates.


Aminomethyl Pyrimidine Ring Diastereoisomer Mixture Minor Diastereoisomer Phosphanylidene 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.


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  1. 1.
    Kincl, F.A., Romo, J., Rosenkranz, G., and Sondheimer, F., J. Chem. Soc., 1956, p. 4163.Google Scholar
  2. 2.
    Mechoulam, R., Sondheimer, F., Melera, A., and Kincl, F.A., J. Am. Chem. Soc., 1961, vol. 83, p. 2022.CrossRefGoogle Scholar
  3. 3.
    Siddigi, S.M., Melman, N., Olah, M.E., Jain, R., Evans, R., Glashofer, M., Radget, W., Cohen, L.A., Daly, J.W., Stiles, G.L., and Jacobson, U.A., Nucleosides Nucleotides, 1996, vol. 15, p. 693.CrossRefGoogle Scholar
  4. 4.
    Yoshida, O., Yasukata, T., Sumino, Y., Munekage, T., Narukawa, Y., and Nishitani, Y., Bioorg. Med. Chem. Lett., 2002, vol. 12, p. 3027.CrossRefGoogle Scholar
  5. 5.
    Potvin, P.G. and Wong, M.H., J. Chem. Soc., Chem. Commun., 1987, p. 672.Google Scholar
  6. 6.
    Narayanan, S., Vangapandu, S., and Jain, R., Bioorg. Med. Chem. Lett., 2001, vol. 11, p. 1133.CrossRefGoogle Scholar
  7. 7.
    Borchers, A. and Schunack, W., Arch. Pharm., 1984, vol. 317, p. 455.CrossRefGoogle Scholar
  8. 8.
    Collman, J.P., Zhong, M., and Costanzo, S., J. Chem. Res., Synop., 2001, no. 5, p. 195.Google Scholar
  9. 9.
    Schlögl, K and Woidich, H., Monatsh. Chem., 1956, vol. 87, p. 679.CrossRefGoogle Scholar
  10. 10.
    Chivikas, C.J. and Hodges, J.C., J. Org. Chem., 1987, vol. 52, p. 3591.CrossRefGoogle Scholar
  11. 11.
    Wade, J.J., J. Heterocycl. Chem., 1986, vol. 23, p. 981.CrossRefGoogle Scholar
  12. 12.
    Kappe, C.O., Tetrahedron, 1993, vol. 49, p. 6937.CrossRefGoogle Scholar
  13. 13.
    Dallinger, D., Stadler, A., and Kappe, C.O., Pure Appl. Chem., 2004, vol. 76, p. 1017.CrossRefGoogle Scholar
  14. 14.
    Zigeuner, G., Hamberger, H., Blasche, H., and Sterk, H., Monatsh. Chem., 1966, vol. 97, p. 1408.CrossRefGoogle Scholar
  15. 15.
    Biginelli, P., Gazz. Chim. Ital., 1893, vol. 23, p. 360.Google Scholar
  16. 16.
    Kappe, C.O., Justus Liebigs Ann. Chem., 1990, p. 505.Google Scholar
  17. 17.
    Molina, P. and Vilaplana, M.J., Synthesis, 1994, no. 12, p. 1197.Google Scholar
  18. 18.
    Palacios, F., Alouso, C., Aparicio, D., Rubiales, G., and de los Santoc, J.M., Tetrahedron, 2007, vol. 63, p. 523.CrossRefGoogle Scholar
  19. 19.
    Molina, P., Díaz, I., and Tárraga, A., Synlett, 1995, no. 10, p. 1031.Google Scholar
  20. 20.
    Ding, M.-W., Tu, H.-Y., and Liu, Z.-J., Synth. Commun., 1997, vol. 27, p. 3657.CrossRefGoogle Scholar
  21. 21.
    Palacios, F., Legido, M., Perez de Heredia, I., Rubiales, G., and Ezpeleta, J.M., Heterocycles, 2001, vol. 55, p. 1641.CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2009

Authors and Affiliations

  • P. S. Lebed’
    • 1
  • P. O. Kos
    • 1
  • V. V. Polovinko
    • 2
  • A. A. Tolmachev
    • 2
  • M. V. Vovk
    • 1
  1. 1.Institute of Organic ChemistryNational Academy of Sciences of UkraineKievUkraine
  2. 2.Enamine Ltd.KievUkraine

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