Skip to main content
SpringerLink
Log in

Synthesis of 2-Aryl-4,5-Bis(Polyfluoroalkyl)Imidazoles from Polyfluoroalkanethiocarboxylic Acid Amides

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Polyfluoroalkanethiocarboxylic acid amides react with aromatic aldehydes with the formation of bis(N-thioacyl)aminals. Treating the latter with acyl chlorides gives 2-aryl-substituted 4,5-bis(polyfluoroalkyl)imidazoles which constitutes a novel method of synthesizing these imidazole derivatives.

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

Fig. 1

Similar content being viewed by others

References

  1. (a) Fluorinated Heterocyclic Compounds: Synthesis, Chemistry, and Applications; Petrov, V. A., Ed.; John Wiley & Sons, Inc.: Hoboken, 2009. (b) Fluorine in Heterocyclic Chemistry; Nenajdenko, V. G., Ed.; Springer Verlag: Berlin, 2013.

  2. (a) Lipunova, G. N.; Nosova, E. V.; Charushin, V. N. Chem. Heterocycl. Compd. 2014, 50, 764. [Khim. Geterotsikl. Soedin. 2014, 831.] (b) Saloutina, L. V.; Zapevalov, A. Ya.; Slepukhin, P. A.; Kodess, M. I.; Saloutin, V. I.; Chupakhin, O. N. Chem. Heterocycl. Compd. 2014, 50, 958. [Khim. Geterotsikl. Soedin. 2014, 1040.]

  3. (a) Khudina, O. G.; Burgart, Ya. V.; Saloutin, V. I. Chem. Heterocycl. Compd. 2014, 50, 856. [Khim. Geterotsikl. Soedin. 2014, 928.] (b) Khudina, O. G.; Ivanova, A. E.; Burgart, Ya. V.; Saloutin, V. I. Chem. Heterocycl. Compd. 2014, 50, 901. [Khim. Geterotsikl. Soedin. 2014, 976.]

  4. Gakh, A. A.; Shermolovich, Yu. G. Curr. Topics Med. Chem. 2014, 14, 952.

    Article  CAS  Google Scholar 

  5. Kirk, K. L. Org. Process Res. Dev. 2008, 12, 305.

    Article  CAS  Google Scholar 

  6. (a) Hagmann, W. K. J. Med. Chem. 2008, 51, 4359. (b) Prakash, G. K. S.; Chacko, S. Curr. Opin. Drug Discovery Dev. 2008, 11, 793.

  7. Davis, F. A.; Kasu, P. V. N. Org. Prep. Proc. Int. 1999, 31, 125.

    Article  CAS  Google Scholar 

  8. Coe, P. L.; Mott, A. W.; Tatlow, J. C. J. Fluorine Chem. 1990, 49, 21.

    Article  CAS  Google Scholar 

  9. Doussot, P.; Portella, C. J. Org. Chem. 1993, 58, 6675.

    Article  CAS  Google Scholar 

  10. Huang, W.-Y.; Liu, Y.-S.; Lu, L. Chin. J. Chem. 1994, 12, 79.

    Article  CAS  Google Scholar 

  11. Elias, A. J.; Hope, H.; Kirchmeier, R. L.; Shreeve, J.-M. Inorg. Chem. 1994, 33, 415.

    Article  CAS  Google Scholar 

  12. Rudnichenko, A. V.; Timoshenko, V. M.; Shermolovich, Yu. G. J. Fluorine Chem. 2004, 125, 439.

    Article  CAS  Google Scholar 

  13. Rudnichenko, A. V.; Kaminskaya, E. I.; Shermolovich, Yu. G. Zh. Org. Farm. Khim., 2006, 4, 38.

    CAS  Google Scholar 

  14. Rudnichenko, A. V.; Shermolovich, Yu. G. Synth. Commun. 2007, 37, 459.

    Article  CAS  Google Scholar 

  15. Мikhailichenko, S. S.; Bouillon, J.-P.; Besson, T.; Shermolovich, Yu. G. Tetrahedron Lett. 2010, 51, 990.

    Article  Google Scholar 

  16. Mykhaylychenko S. S.; Pikun, N. V.; Rusanov, E. B.; Shermolovich, Yu. G. J. Fluorine Chem. 2014, 168, 105.

    Article  CAS  Google Scholar 

  17. Bernthsen, A. Justus Liebigs Ann. Chem. 1878, 192, 1.

    Article  Google Scholar 

  18. Wijma, J.; van Daalen, J. J.; Daams, J.; van Deursen, F. W. J. Agr. Food Chem. 1970, 18, 674.

    Article  CAS  Google Scholar 

  19. Shabana, R.; El-Kateb, A. A. Pol. J. Chem. 1983, 57, 647.

    CAS  Google Scholar 

  20. Goerdeler, J.; Horstmann, H. Chem. Ber. 1960, 93, 663.

    Article  CAS  Google Scholar 

  21. Heil, M.; Lui, N.; Marchold, A.; Erdelen, C.; Wachendorff-Neumann, U.; Turberg, A.; Mencke, N. WO Patent 9517390.

  22. Kamitori, Y. Tetrahedron Lett. 2000, 41, 9267.

    Article  CAS  Google Scholar 

  23. Timoshenko, V. M.; Rudnichenko, A. V.; Tkachenko, A. V.; Shermolovich Yu. G. Russ. J. Org. Chem. 2005, 41, 268. [Zh. Org. Khim., 2005, 41, 277.]

    Article  CAS  Google Scholar 

  24. Sheldrick, G. M. SADABS – Program for Scaling and Correction of Area Detector Data, University of Göttingen, Germany, 1996.

    Google Scholar 

  25. Sheldrick, G. M. Acta Crystallogr., Sect. A: Found. Crystallogr. 2008, A64, 112.

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Murmanska St., Kyiv, 02660, Ukraine

    Sergey S. Mykhaylychenko, Nadezhda V. Pikun, Eduard B. Rusanov & Yuriy G. Shermolovich

Authors
  1. Sergey S. Mykhaylychenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Nadezhda V. Pikun
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Eduard B. Rusanov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Yuriy G. Shermolovich
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Yuriy G. Shermolovich.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2015, 51(2), 128–132

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Mykhaylychenko, S.S., Pikun, N.V., Rusanov, E.B. et al. Synthesis of 2-Aryl-4,5-Bis(Polyfluoroalkyl)Imidazoles from Polyfluoroalkanethiocarboxylic Acid Amides. Chem Heterocycl Comp 51, 128–132 (2015). https://doi.org/10.1007/s10593-015-1669-6

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-015-1669-6

Keywords

Search

Navigation