Skip to main content
SpringerLink
Log in

Catalytic hydrogenation of methyl 3,4-diazatricyclo-[5.2.1.02,6]dec-4-ene-5-carboxylate

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

The hydrogenation at Raney nickel of the pyrazoline ring in methyl exo-3,4-diazatricyclo-[5.2.1.02,6]dec-4-ene-5-carboxylate takes place quantitatively with the preferential formation of the trans isomer of 5-amino-exo-3-azatricyclo[5.2.1.02,6]decan-4-one. The 3-methoxycarbonylmethyl-, 3-acetyl-, and 3-nitroso-substituted esters are not hydrogenated under these conditions.

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. A. N. Kost, G. A. Golubeva, and R. G. Stepanov, Zh. Obshch. Khim., 32, 2240 (1962).

    CAS  Google Scholar 

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

    CAS  Google Scholar 

  3. А. Otto, B. Ziemer, and Y. Liebscher, Synthesis, 965 (1999).

  4. H. Sasaki and E. M. Carreira, Synthesis, 135 (2000).

  5. I. V. Kostyuchenko, E. V. Shulishov, V. A. Korolev, and V. A. Dokichev, Izv. Akad. Nauk, Ser. Khim., 2482 (2005).

  6. 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 

  7. 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. Nefëdov, RF Pat. 2281938; Byul. Izobr., No. 23 (2006).

  8. A. Lebedev, Khim. Geterotsikl. Soedin., 803 (2007). [Chem. Heterocycl. Comp., 43, 673 (2007)].

  9. J. G. Hardman, L. E. Limbird, A. G. Gilman (editors), Goodman and Gilman’s Pharmacological Basis of Therapeutics, 10th ed., McGraw-Hill, New York, 2001.

    Google Scholar 

  10. F. Felluga, V. Gombac, G. Pitacco, and E. Valentin, Tetrahedron: Asymmetry, 15, 3323 (2004).

    Article  CAS  Google Scholar 

  11. F. Felluga, V. Gombac, G. Pitacco, and E. Valentin, Tetrahedron: Asymmetry, 16, 1341 (2005).

    Article  CAS  Google Scholar 

  12. D. Gunn, C. Akuche, J. Baryza, and M.-L. Blue, Bioorg. Med. Chem. Lett., 15, 3053 (2005).

    Article  CAS  Google Scholar 

  13. J. Clayden, F. E. Knowles, and I. R. Baldwin, J. Am. Chem. Soc., 127, 2412 (2005).

    Article  CAS  Google Scholar 

  14. V. Singh, R. Saxena, and S. Batra, J. Org. Chem., 70, 353 (2005).

    Article  CAS  Google Scholar 

  15. X. Zhou, W. Liu, J. Ye, and P. Huang, J. Org. Chem., 72, 8904 (2007).

    Article  CAS  Google Scholar 

  16. C. T. Hoang, V. H. Nguyen, V. Alezra, and C. Kouklovsky, J. Org. Chem., 73, 1162 (2008).

    Article  CAS  Google Scholar 

  17. V. A. Gorpinchenko, D. V. Petrov, L. V. Spirikhin, V. A. Dokichev, and Yu. V. Tomilov, Zh. Org. Khim., 42, 1706 (2006).

    CAS  Google Scholar 

  18. E. A. Shafikova, D. V. Petrov, and V. A. Dokichev, Khim. Geterotsikl. Soedin., 533 (2007). [Chem. Heterocycl. Comp., 43, 434 (2007)].

    Google Scholar 

  19. S. Murakami, T. Harada, and A. Tai, Bull. Chem. Soc. Jрn., 53, 1356 (1980).

    Article  CAS  Google Scholar 

  20. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, A. G. Baboul, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, J. L. Andres, C. Gonzalez, M. Head-Gordon, E. S. Replogle, and J. A. Pople, GAUSSIAN 98 (Revision A.7), Gaussian, Inc., Pittsburgh (PA), 1998.

    Google Scholar 

  21. V. Barone and M. Cossi, J. Phys. Chem., A, 102, 1995 (1998).

    Article  CAS  Google Scholar 

  22. J. Flisinska, S. Lesniak, and R. Nazarski, Tetrahedron, 60, 8181 (2004).

    Article  Google Scholar 

  23. G. V. Mock, US Pat. 3187051; Ref. Zh. Khim, 13Н77 П (1966).

  24. V. Poroikov and D. Filimonov, in: Christoph Helma (editor), PASS: Prediction of Biological Activity Spectra for Substances. Predictive Toxicology, Marcel Dekker, New York, 2005, p. 459.

    Google Scholar 

Download references

Author information

Authors and Affiliations

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

    V. A. Gorpinchenko, D. V. Petrov, S. L. Khursan & V. A. Dokichev

  2. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, 119991, Russia

    Yu. V. Tomilov

Authors
  1. V. A. Gorpinchenko
    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. S. L. Khursan
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. V. A. Dokichev
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Yu. V. Tomilov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to V. A. Dokichev.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1301–1310, September, 2009.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Gorpinchenko, V.A., Petrov, D.V., Khursan, S.L. et al. Catalytic hydrogenation of methyl 3,4-diazatricyclo-[5.2.1.02,6]dec-4-ene-5-carboxylate. Chem Heterocycl Comp 45, 1039–1046 (2009). https://doi.org/10.1007/s10593-009-0389-1

Download citation

  • Received:

  • Revised:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-009-0389-1

Keywords

Search

Navigation