Skip to main content
Log in

Synthesis and structure of new 3,7-diazabicyclo[3.3.1]nonane derivatives

  • Full Articles
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

Aminomethylation of triethylammonium 4-aryl-3,5-dicyano-6-oxo-1,4,5,6-tetrahydropyridin-2-olates and their sulfur and selenium analogs, as well as the structure of formed products, were studied in details. The reaction is of general character and leads to the formation of 7-substituted 9-aryl-2,4-dioxo-, 9-aryl-4-oxo-2-thioxo-, 9-aryl-4-oxo-2-selenoxo-3,7-diazabicyclo[3.3.1]nonane derivatives or their salts. The structures of ethyl 9-(2-chlorophenyl)-5-cyano-7-(4-methylphenyl)-2-oxo-4-thioxo-3,7-diazabicyclo[3.3.1]nonane-1-carboxylate (as a complex with N-methylmorpholine) and triethylammonium salt of 7-benzyl-4-oxo-2-selenoxo-9-(2-thienyl)-3,7-diazabicyclo[3.3.1]nonane-1,5-dicarbonitrile were studied by X-ray crystallography.

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

Access this article

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. N. S. Zefirov, S. V. Rogozina, Russ. Chem. Rev., 1973, 42, 190.

    Article  Google Scholar 

  2. R. Jeyaraman, S. Avila, Chem. Rev., 1981, 81, 149.

    Article  CAS  Google Scholar 

  3. N. S. Zefirov, V. A. Palyulin, Top. Stereochem., 1991, 20, 171.

    Article  CAS  Google Scholar 

  4. G. L. Garrison, K. D. Berlin, B. J. Scherlag, R. Lazzara, E. Patterson, T. Fazekas, S. Sangiah, C. L. Chen, F. D. Schubot, D. van der Helm, J. Med. Chem., 1996, 39, 2559.

    Article  CAS  Google Scholar 

  5. G. S. Smith, M. D. Thompson, K. D. Berlin, E. M. Holt, B. J. Scherlag, E. Patterson, R. Lazzara, Eur. J. Med. Chem., 1990, 25, 1.

    Article  CAS  Google Scholar 

  6. B. Kцgel, T. Christoph, E. Fridericks, H. H. Hennies, T. Mathiesen, J. Schneider, U. Holzgrabe, CNS Drug Rev., 1998, 4, 54

    Article  Google Scholar 

  7. U. Kuhl, W. Englberger, M. Haurand, U. Holzgrabe, Arch. Pharm., 2000, 333, 226

    Article  CAS  Google Scholar 

  8. T. Siener, A. Cambareri, U. Kuhl, W. Englberger, M. Haurand, B. Kögel, U. Holzgrabe, J. Med. Chem., 2000, 43, 3746

    Article  CAS  Google Scholar 

  9. U. Kuhl, M. von Korff, K. Baumann, C. Burschka, U. Holzgrade, J. Chem. Soc., Perkin Trans. 2, 2001, 2037

    Google Scholar 

  10. U. Holzgrabe, W. Brandt, J. Med. Chem., 2003, 46, 1383

    Article  CAS  Google Scholar 

  11. Y. Wang, K. Tang, S. Inan, D. Siebert, U. Holzgrabe, D. Y. W. Lee, P. Huang, J.-G. Li, A. Cowan, L.-Y. Liu-Chen, J. Pharmacol. Exp. Therap., 2005, 312, 220.

    Article  CAS  Google Scholar 

  12. S. Z. Vatsadze, V. S. Tyurin, N. V. Zyk, A. V. Churakov, L. G. Kuz´mina, E. V. Avtomonov, R. D. Rakhimov, K. P. Butin, Russ. Chem. Bull. (Int. Ed.), 2005, 54, 1825 [Izv. Akad. Nauk, Ser. Khim., 2005, 1773]

    Article  CAS  Google Scholar 

  13. P. Comba, H. Pritzkow, W. Schiek, Angew. Chem., Int. Ed., 2001, 40, 2465.

    Article  CAS  Google Scholar 

  14. P. Comba, B. Nuber, A. Ramlow, J. Chem. Soc. Dalton Trans., 1997, 347.

    Google Scholar 

  15. P. Comba, B. Kanellakopulos, Ch. Katsichtis, A. Lienke, H. Pritzkow, F. Rominger, J. Chem. Soc. Dalton Trans., 1998, 3997.

    Google Scholar 

  16. D. St. C. Black, G. B. Deacon, M. Rose, Tetrahedron, 1995, 51, 2005.

    Google Scholar 

  17. M. R. Bukowski, P. Comba, A. Lienke, C. Limberg, C. Lopez de Laorden, R. Mas-Ballestй, M. Merz, L. Que, Angew. Chem., Int. Ed., 2006, 45, 3446.

    Article  CAS  Google Scholar 

  18. M. Haberberger, C. I. Someya, A. Company, E. Irran, S. Enthaler, Catalysis Lett., 2012, 142, 557.

    Article  CAS  Google Scholar 

  19. P. Comba, Y.-M. Lee, W. Namb, A. Waleska, Chem. Commun., 2014, 50, 412.

    Article  CAS  Google Scholar 

  20. E. A. Chigorina, V. V. Dotsenko, Chem. Heterocycl. Compd. (Engl. Transl.), 2012, 48, 1722 [Khim. Geterotsikl. Soedin., 2012, 1838].

    Article  Google Scholar 

  21. V. V. Dotsenko, S. G. Krivokolysko, V. P. Litvinov, Chem. Heterocycl. Compd. (Engl. Transl.), 2005, 41, 1428 [Khim. Geterotsikl. Soedin., 2005, 1695].

    Article  CAS  Google Scholar 

  22. V. V. Dotsenko, S. G. Krivokolysko, V. P. Litvinov, Monatsh. Chem., 2007, 138, 489.

    Article  CAS  Google Scholar 

  23. V. V. Dotsenko, S. G. Krivokolysko, V. P. Litvinov, Russ. Chem. Bull. (Int. Ed.), 2007, 56, 2482 [Izv. Akad. Nauk, Ser. Khim., 2007, 2397].

    Article  CAS  Google Scholar 

  24. V. V. Dotsenko, S. G. Krivokolysko, V. P. Litvinov, Chem. Heterocycl. Compd. (Engl. Transl.), 2015, 51, 109 [Khim. Geterotsikl. Soedin., 2015, 51, 109].

    Article  CAS  Google Scholar 

  25. V. V. Dotsenko, K. A. Frolov, S. G. Krivokolysko, Chem. Heterocycl. Compd. (Engl. Transl.), 2013, 49, 657 [Khim. Geterotsikl. Soedin., 2013, 705].

    Article  CAS  Google Scholar 

  26. K. A. Frolov, V. V. Dotsenko, S. G. Krivokolysko, V. P. Litvinov, Chem. Heterocycl. Compd. (Engl. Transl.), 2012, 48, 442 [Khim. Geterotsikl. Soedin., 2012, 471].

    Article  CAS  Google Scholar 

  27. Structure Correlation, Eds H.-B. Burgi, J. D. Dunitz, Verlag Chemie, Weinheim, 1994, Vol. 2, p. 741.

  28. V. V. Dotsenko, K. A. Frolov, S. G. Krivokolysko, E. A. Chigorina, T. M. Pekhtereva, S. Yu. Suykov, E. S. Papayanina, A. O. Dmitrienko, I. S. Bushmarinov, Chem. Heterocycl. Compd. (Engl. Transl.), 2016, 52, 116 [Khim. Geterotsikl. Soedin., 2016, 52, 116].

    Article  CAS  Google Scholar 

  29. E. A. Chigorina, V. V. Dotsenko, S. G. Krivokolysko, Chem. Heterocycl. Compd. (Engl. Transl.), 2011, 47, 913 [Khim. Geterotsikl. Soedin., 2011, 1108]

    Article  CAS  Google Scholar 

  30. E. A. Chigorina, Chem. Heterocycl. Compd. (Engl. Transl.), 2013, 49, 574 [Khim. Geterotsikl. Soedin., 2013, 615].

    Article  CAS  Google Scholar 

  31. V. D. Dyachenko, Yu. A. Sharanin, S. G. Krivokolysko, Russ. J. Org. Chem. (Engl. Transl.), 1995, 31, 136 [Zh. Org. Khim., 1995, 31, 149]

    Google Scholar 

  32. S. G. Krivokolysko, V. D. Dyachenko, V. N. Nesterov, Yu. A. Sharanin, Yu. T. Struchkov, Zh. Org. Khim., 1999, 35, 966 [Russ. J. Org. Chem. (Engl. Transl.), 1999, 35]

    Google Scholar 

  33. S. G. Krivokolysko, V. D. Dyachenko, V. P. Litvinov, Russ. Chem. Bull. (Int. Ed.), 2000, 49, 487 [Izv. Akad. Nauk, Ser. Khim., 2000, 485].

    Article  CAS  Google Scholar 

  34. G. Sheldrick, Acta Cryst. Sect. A, 2008, 64, 112.

    Article  CAS  Google Scholar 

  35. O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard, H. Puschmann, J. Appl. Cryst., 2009, 42, 339.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to E. A. Chigorina.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 2260—2269, September, 2016.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Chigorina, E.A., Frolov, K.A., Dotsenko, V.V. et al. Synthesis and structure of new 3,7-diazabicyclo[3.3.1]nonane derivatives. Russ Chem Bull 65, 2260–2269 (2016). https://doi.org/10.1007/s11172-016-1576-8

Download citation

  • Received:

  • Revised:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-016-1576-8

Key words

Navigation