Skip to main content
SpringerLink
Log in

Reactions of aromatic and heteroaromatic β-amino-β-polyfluoroalkylvinyl ketones with ethylenediamine. A new synthesis ofN,N′-unsubstituted imidazolidines

  • Organic Chemistry
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

The reactions of aromatic and heteroaromatic β-amino-β-polyfluoroalkylvinyl ketones with ethylenediamine results in the formation of 2,3-dihydro-1H-1,4-diazepines,N,N′-unsubstituted imidazolidines, orN,N′-ethylenebis(aminovinyl ketones). The reaction route depends on the reaction conditions, the nature of the substituent at the carbonyl group, and the number of fluorine atoms in the polyfluoroalkyl radical.

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. C. Kashima and Y. Yamamoto,Bull. Chem. Soc. Jpn., 1979,52, 1735.

    Article  CAS  Google Scholar 

  2. K. I. Pashkevich and V. I. Filyakova,Izv. Akad. Nauk SSSR, Ser. Khim., 1986, 620 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1986,35 (Engl. Transl.)].

    Google Scholar 

  3. M. Hojo, R. Masuda, E. Okada, S. Sakaguchi, H. Narumiya, and K. Morimoto,Tetrahedron Lett., 1989,30, 6173.

    Article  CAS  Google Scholar 

  4. K. I. Pashkevich, A. Ya. Aizikovich, and I. Ya. Postovskii,Izv. Akad. Nauk SSSR, Ser. Khim., 1981, 455 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1981,30 (Engl. Transl.)].

    Google Scholar 

  5. V. Ya. Sosnovskikh and M. Yu. Mel'nikov,Mendeleev Commun., 1998, 19.

  6. V. Ya. Sosnovskikh, M. Yu. Mel'nikov, and I. A. Kovaleva,Izv. Akad. Nauk, Ser. Khim., 1998, 2305 [Russ. Chem. Bull., 1998,47, 2234 (Engl. Transl.)].

  7. H. W. Wanzlick and W. Lochel,Chem. Ber., 1953,86, 1463.

    Article  CAS  Google Scholar 

  8. T. H. Fife and J. E. C. Hutchins,J. Am. Chem. Soc., 1976,98, 2536.

    Article  CAS  Google Scholar 

  9. J. A. Durden, Jr. and D. L. Heywood,J. Org. Chem., 1968,33, 3932.

    Article  CAS  Google Scholar 

  10. M. M. Joullie, G. M. J. Slusarczuk, A. S. Dey, P. B. Venuto, and R. H. Yocum,J. Org. Chem., 1967,32, 4103.

    Article  CAS  Google Scholar 

  11. V. A. Sedavkina, I. V. Lizak, and N. N. Sorokin,Khim. Geterotsikl. Soedin., 1987, 1405 [Chem. Heterocycl. Compd., 1987 (Engl. Transl.)].

  12. T. S. Sulkowski, M. A. Wille, A. Mascitti, and J. L. Diebold,J. Org. Chem., 1967,32, 2180.

    Article  CAS  Google Scholar 

  13. G. M. J. Slusarczuk and M. M. Joullie,J. Org. Chem., 1971,36, 37.

    Article  Google Scholar 

  14. G. Crank, D. R. K. Harding, and S. S. Szinai,J. Med. Chem., 1970,13, 1212.

    Article  CAS  Google Scholar 

  15. G. Crank, D. R. K. Harding, and S. S. Szinai,J. Med. Chem., 1970,13, 1215.

    Article  CAS  Google Scholar 

  16. N. P. Stepanova, V. B. Lebedeva, N. A. Orlova, E. S. Turbanova, and A. A. Petrov,Zh. Org. Khim., 1988,24, 692, [J. Org. Chem., 1988,24 (Engl. Transl.)].

    CAS  Google Scholar 

  17. A. V. Fokin, A. F. Kolomiets, and N. V. Vasil'ev,Usp. Khim., 1984,53, 398, [Russ. Chem. Rev., 1984,53 (Engl. Transl.)].

    CAS  Google Scholar 

  18. V. Ya. Sosnovskikh and M. Yu. Morozov,Khim. Geterotsikl. Soedin., 1998, 847 [Chem. Heterocycl. Compd., 1998 (Engl. Transl.)].

  19. V. Ya. Sosnovskikh and I. S. Ovsyannikov,Zh. Org. Khim., 1990,26, 2086 [J. Org. Chem., 1990,26 (Engl. Transl.)].

    Google Scholar 

  20. K. I. Pashkevich, A. Ya. Aizikovich, M. N. Rudaya, V. V. Mosin, and I. Ya. Postovskii,Izv. Akad. Nauk SSSR, Ser. Khim., 1980, 1939 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1980,29 (Engl. Transl.)].

  21. A. F. Kluge and C. P. Lillya,J. Org. Chem., 1971,36, 1977.

    Article  Google Scholar 

  22. Z. E. Skryabina, Ya. V. Burgart, and V. I. Saloutin,Izv. Akad. Nauk SSSR, Ser. Khim., 1991, 890 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1991,40, 788 (Engl. Transl.)].

    Google Scholar 

  23. M. F. Richardson and R. E. Sievers,J. Inorg. Nucl. Chem., 1970,32, 1895.

    Article  CAS  Google Scholar 

  24. H. A. Staab and F. Vogtle,Chem. Ber., 1965,98, 2701.

    CAS  Google Scholar 

  25. G. O. Dudek,J. Am. Chem. Soc., 1963,85, 694.

    Article  CAS  Google Scholar 

  26. G. O. Dudek and R. H. Holm,J. Am. Chem. Soc., 1962,84, 2691.

    Article  CAS  Google Scholar 

  27. V. Ya. Sosnovskikh,Mendeleev Commun., 1996, 189.

  28. V. Ya. Sosnovskikh, V. A. Kutsenko, and M. Yu. Morozov,Mendeleev Commun., 1998, 126.

  29. G. O. Dudek and R. H. Holm,J. Am. Chem. Soc., 1961,83, 2099.

    Article  CAS  Google Scholar 

  30. V. I. Filyakova, I. G. Busygin and K. I. Pashkevich,Zh. Org. Khim., 1989,25, 1865 [J. Org. Chem., 1989,25 (Engl. Transl.)].

    CAS  Google Scholar 

  31. V. Ya. Sosnovskikh and I. S. Ovsyannikov,Zh. Org. Khim., 1993,29, 89 [J. Org. Chem., 1993,29 (Engl. Transl.)].

    CAS  Google Scholar 

  32. K. I. Pashkevich, V. I. Saloutin, and I. Ya. Postovskii,Usp. Khim., 1981,50, 325 [Russ. Chem. Rev., 1981,50 (Engl. Transl.)].

    CAS  Google Scholar 

  33. A. M. Gorringe, D. Lloyd, and D. R. Marshall,J. Chem. Soc., (C), 1967, 2340.

Download references

Author information

Authors and Affiliations

  1. A. M. Gorky Ural State University, 51 prosp. Lenina, 620083, Ekaterinburg, Russian Federation

    V. Ya. Sosnovskikh & V. A. Kutsenko

Authors
  1. V. Ya. Sosnovskikh
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. V. A. Kutsenko
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 546–556, March, 1999.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Sosnovskikh, V.Y., Kutsenko, V.A. Reactions of aromatic and heteroaromatic β-amino-β-polyfluoroalkylvinyl ketones with ethylenediamine. A new synthesis ofN,N′-unsubstituted imidazolidines. Russ Chem Bull 48, 540–551 (1999). https://doi.org/10.1007/BF02496176

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02496176

Key words

Search

Navigation