Skip to main content
SpringerLink
Log in

Synthesis of norbornane series tetra- and hexahydropyrimidines

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Condensation of exo-2-amino-exo-3-aminomethylnorbornane with acetone, methyl cyclopropyl ketone, cyclohexanone, urea, and formic, acetic, and benzoic acids gave norbornane series tetra- and hexa-hydropyrimidines. It was found that 4-cyclopropyl-4-methyl-exo-3,5-diazatricyclo[6.2.1.02,7]undecane and 4-methyl-exo-3,5-diazatricyclo[6.2.1.02,7]undec-3-ene show analgesic activity.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. M. D. Mashkovskii, Drugs [in Russian], Vol. 1, Meditsina, Moscow (1998), p. 2.

    Google Scholar 

  2. J. Einsiedel, H. Hubner, and P. Gmeiner, Bioorg. Med. Chem. Lett., 13, 851 (2003).

    Article  CAS  Google Scholar 

  3. T. Prisinzano, H. Law, M. Dukat, A. Slassi, N. MaClean, L. Demchyshyn, and A. Glennon, Bioorg. Med. Chem. Lett., 9, 613 (2001).

    Article  CAS  Google Scholar 

  4. A. Zamri, F. Sirockin, and M. A. Abdallah, Tetrahedron, 55, 5157 (1999).

    Article  CAS  Google Scholar 

  5. D. Scholz, P. Hecht, H. Schmidt, and A. Billich, Monatsh. Chem., 130, 1283 (1999).

    CAS  Google Scholar 

  6. L. Zhang, L. Xu, and C. U. Kim, Tetrahedron Lett., 44, 5871 (2003).

    Article  CAS  Google Scholar 

  7. J. D. Clark, J. T. Collins, H. P. Kleine, G. A. Weisenburger, and D. K. Anderson, Org. Process Res. Dev., 8, 571 (2004).

    Article  CAS  Google Scholar 

  8. W. S. Messer, Jr., Y. F. Abuh, Y. Liu, S. Periyasamy, D. O. Ngur, M. A. N. Edgar, A. A. El-Assadi, S. Sbeih, P. G. Dunbar, S. Roknich, T. Rho, Z. Fang, B. Ojo, H. Zhang, J. J. Huzl, III, and P. I. Nagy, J. Med. Chem., 40, 1230 (1997).

    Article  CAS  Google Scholar 

  9. A. R. Katritzky, S. K. Singh, and H.-Y. He, J. Org. Chem., 67, 3115 (2002).

    Article  CAS  Google Scholar 

  10. F. Qian, J. E. McCusker, Y. Zhang, A. D. Main, M. Chlebowski, M. Kokka, and L. McElwee-White, J. Org. Chem., 67, 4086 (2002).

    Article  CAS  Google Scholar 

  11. E. A. Muravyova, S. M. Desenko, V. I. Musatov, I. V. Knyazeva, S. V. Shishkina, O. V. Shishkin, and V. A. Chebanov, J. Comb. Chem., 9, 797 (2007).

    Article  CAS  Google Scholar 

  12. D. V. Petrov, V. A. Gorpinchenko, E. A. Shafikova, F. S. Zarudii, N. Zh. Baschenko, R. Yu. Khisamutdinova, N. S. Makara, V. A. Vakhitov, Yu. V. Vakhitova, Chzhan Veimu, R. I. Alimbekov, V. A. Dokichev, Yu. V. Tomilov, and O. M. Nefedov, Russian Pat. 2281938; Byul. Izobr., No. 23 (2006).

  13. V. A. Gorpinchenko, E. A. Yatsynich, D. V. Petrov, L. T. Karachurina, R. Yu. Khisamutdinova, N. Zh. Baschenko, V. A. Dokichev, Yu. V. Tomilov, M. S. Yunusov, and O. M. Nefedov, Khim. -Farm. Zh., 39, No. 6, 9 (2005).

    Google Scholar 

  14. L. I. Kas’yan, O. T. Zlenko, V. I. Mamchur, A. O. Kas’yan, and I. M. Tarabara, Farm. Zhurn., 59 (2002).

  15. A. Esanu, Belgian Pat. 902231; Chem. Abstr., 104, 110121 (1986).

  16. R. B. Moodie, M. Z. Moustras, G. Read, and J. P. B. Sandall, J. Chem. Soc., Perkin Trans. 2, 169 (1997).

  17. J. B. Lambert and M. N. Majchrsak, J. Am. Chem. Soc., 102, 3588 (1980).

    Article  CAS  Google Scholar 

  18. A. Goblios, L. Lazar, and F. Fulop, Tetrahedron, 58, 1011 (2002).

    Article  Google Scholar 

  19. O. Sato, M. Seshimo, and J. Tsunetsugu, J. Chem. Res., Synop., 568 (1998).

  20. E. A. Yatsynich, D. V. Petrov, V. A. Dokichev, and Yu. V. Tomilov, Zh. Org. Khim., 41, 1187 (2005).

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Organic Chemistry Institute, Ufa Scientific Center of the Russian Academy of Sciences, Ufa, 450054, Russia

    E. A. Shafikova, D. V. Petrov, T. A. Sapozhnikova, N. J. Baschenko & V. A. Dokichev

Authors
  1. E. A. Shafikova
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. D. V. Petrov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. T. A. Sapozhnikova
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. N. J. Baschenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. V. A. Dokichev
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to D. V. Petrov.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 862–867, June, 2009.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Shafikova, E.A., Petrov, D.V., Sapozhnikova, T.A. et al. Synthesis of norbornane series tetra- and hexahydropyrimidines. Chem Heterocycl Comp 45, 685–690 (2009). https://doi.org/10.1007/s10593-009-0328-1

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-009-0328-1

Keywords

Search

Navigation