Skip to main content
Log in

Synthesis of fluorine-containing heterocycles based on polyfluorooxiranes and O,N,S-dinucleophiles

  • Reviews
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

The methods of synthesis of fluorine-containing O, N, S-heterocyclic compounds, such as diazines, oxazines, thiazolines, oxazolines, quinoxalines, benzoxazines, benzothiazines, imidazolidines, and glycolurils, based on the reactions of perfluoro- and polyfluorooxiranes with bifunctional nucleophilic reagents, are presented in the review. Significant influence of the solvent nature on the composition and structure of the obtained compounds is demonstrated.

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.

Similar content being viewed by others

References

  1. JP Pat. 128769; Chem. Abstrs, 2002, 136, 340675n.

  2. Zhu Xiaoxiang, Yu. Qian-sheng, R. G. Cutler, C. W. Culmsee, H. W. Holloway, D. K. Lahiri, M. P. Mattson, N. H. Greig, J. Med. Chem., 2002, 45, 5090.

    Article  Google Scholar 

  3. F. Schiaffella, A. Macchiarulo, L. Milanese, A. Vecchiarelli, G. Costantino, D. Pietrella, R. Fringuelli, J. Med. Chem., 2005, 48, 7658.

    Article  CAS  Google Scholar 

  4. C. G. Mortimer, G. Wells, J.-P. Crochard, E. L. Stone, D. Bradshaw, J. Med. Chem., 2006, 49, 179.

    Article  CAS  Google Scholar 

  5. M. D. Мashkovsky, Lekarstvennie sredstva [Drugs], Novaya Volna, Moscow, 2002, 1, 39, 86 (in Russian).

    Google Scholar 

  6. S. S. Novikov, Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.), 1979, 28, 2083 [Izv. Akad. Nauk SSSR, Ser. Khim., 1979, 2261].

    Article  Google Scholar 

  7. О. V. Lebedev, L. I. Chmelnitsky, L. V. Epishina, L. I. Suvorova, I. V. Zaikonnikova, I. Е. Zimakova, S. V. Kirshin, А. М. Karpov, V. S. Chudnovsky, М. V. Povstyanoi, V. А. Eres´ko, in Tselenapravlennyi poisk novykh neurotropnykh preparatov [Directional Search for New Neurotropic Drugs], Zinatve, Riga, 1983, 81 (in Russian).

    Google Scholar 

  8. DE Pat. 19 918297; Chem. Abstrs, 2000, 133, 309911a.

  9. US Pat. 6281168; Chem. Abstrs, 2001, 135, 191661e.

  10. EP Pat. 686345; Chem. Abstrs, 1996, 124, 79471q.

  11. EP Pat. 262428; Chem. Abstrs, 1988, 109, 93010k.

  12. P. Tarrant, C. G. Allison, K. P. Barthold, Fluor. Chem. Rev., 1971, 5, 77.

    CAS  Google Scholar 

  13. H. Millauer, W. Schwertfeger, G. Siegemund, Angew. Chem., 1985, 97, 164.

    Article  CAS  Google Scholar 

  14. N. Ishikawa, Novoe v technologii soiedinenii ftora [Fluorine Compounds. Modern Technology and Application], Ed. N. Ishikawa, Mir, Moscow, 1984, p. 21 (in Russian).

  15. G. G. Furin, Ftorsoderzhashchie heterotsiclicheskie soedineniya. Sintez i primenenie [Fluorocontaining Heterocyclic Compounds, Synthesis and Application], Nauka, Novosibirsk, 2001, 183 pp. (in Russian).

    Google Scholar 

  16. I. L. Knunyants, V. V. Shokina, I. V. Galakhov, Chem. Heterocycl. Compd. (Engl. Transl.), 1966, 666 [Khim. Geterotsikl. Soedin., 1966, 873].

    Google Scholar 

  17. N. Ishikawa, S. Sasaki, Bull. Chem. Soc. Jpn, 1977, 50, 2164.

    Article  CAS  Google Scholar 

  18. H. Kawa, H. A. Hamouda, N. Ishikawa, Bull. Chem. Soc. Jpn, 1980, 53, 1694.

    Article  CAS  Google Scholar 

  19. I. P. Kolenko, T. I. Filyakova, A. Ya. Zapevalov, E. P. Lur´e, Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.), 1979, 28, 2323 [Izv. Akad. Nauk SSSR, Ser. Khim., 1979, 2509].

    Article  Google Scholar 

  20. UK Pat. 904877; Сhem. Аbstrs, 1963, 58, 12513b.

  21. L. V. Saloutina, A. Ya. Zapevalov, M. I. Kodess, V. I. Saloutin, J. Fluor. Chem., 1998, 87, 49.

    Article  CAS  Google Scholar 

  22. L. V. Saloutina, A. Ya. Zapevalov, V. I. Saloutin, P. A. Slepukhin, M. I. Kodess, V. E. Kirichenko, M. G. Pervova, O. N. Chupakhin, J. Fluor. Chem., 2007, 128, 769.

    Article  CAS  Google Scholar 

  23. L. V. Saloutina, A. Ya. Zapevalov, M. I. Kodess, V. I. Saloutin, O. N. Chupakhin, Mendeleev Commun., 1999, 231.

    Google Scholar 

  24. L. V. Saloutina, A. Ya. Zapevalov, M. I. Kodess, V. I. Saloutin, G. G. Aleksandrov, O. N. Chupakhin, J. Fluor. Chem., 2000, 104, 155.

    Article  CAS  Google Scholar 

  25. S. V. Usol´tseva, G. P. Andronnikova, V. S. Mokrushin, Chem. Heterocycl. Compd. (Engl. Transl.), 1991, 27, 343 [Khim. Geterotsikl. Soedin., 1991, 435].

    Article  Google Scholar 

  26. L. V. Saloutina, A. Ya. Zapevalov, M. I. Kodess, K. A. Lyssenko, M. Yu. Antipin, V. I. Saloutin, O. N. Chupakhin, J. Fluor. Chem., 2003, 120, 41.

    Article  CAS  Google Scholar 

  27. L. V. Saloutina, A. Ya. Zapevalov, V. I. Saloutin, P. A. Slepukhin, M. I. Kodess, V. E. Kirichenko, M. G. Pervova, O. N. Chupakhin, J. Fluor. Chem., 2007, 128, 769.

    Article  CAS  Google Scholar 

  28. L. V. Saloutina, A. Ya. Zapevalov, V. I. Saloutin, P. A. Slepukhin, M. I. Kodess, O. N. Chupakhin, J. Fluor. Chem., 2009, 130, 853.

    Article  CAS  Google Scholar 

  29. L. V. Saloutina, A. Ya. Zapevalov, M. I. Kodess, P. A. Slepukhin, V. I. Saloutin, O. N. Chupakhin, J. Fluor. Chem., 2012, 139, 16.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to V. I. Saloutin.

Additional information

Based on the materials of the IV all-Russian Conference on Organic Chemistry and the XVIII Youth School-Conference on Organic Chemistry (November 22—27, 2015, Moscow, Russia).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 2163—2171, September, 2016.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Saloutin, V.I., Saloutina, L.V., Zapevalov, A.Y. et al. Synthesis of fluorine-containing heterocycles based on polyfluorooxiranes and O,N,S-dinucleophiles. Russ Chem Bull 65, 2163–2171 (2016). https://doi.org/10.1007/s11172-016-1564-z

Download citation

  • Received:

  • Revised:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-016-1564-z

Key words

Navigation