Skip to main content
SpringerLink
Log in

Synthesis of 5-(polyfluoroalkyl)-1,3-thiazolidines from polyfluoroalkanethiocarboxylic acid derivatives

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Novel 5-(polyfluoroalkyl)-1,3-thiazolidines were synthesized by the reaction of polyfluoroalkanethiocarboxylic acid derivatives with azomethine ylide, generated in situ via acid-catalyzed desilylation of N-benzyl-N-(methoxymethyl)-N-[(trimethylsilyl)methyl]amine.

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) 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: Heidelberg, New York, London, 2014. (c) Gakh, A. A.; Shermolovich, Yu. Curr. Top. Med. Chem. 2014, 14, 952. (d) Wang, J.; Sánchez-Roselló, M.; Aceña, J. L.; del Pozo, C.; Sorochinsky, A. E.; Fustero, S.; Soloshonok, V. A.; Liu, H. Chem. Rev. 2014, 114, 2432.

  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.] (c) Mykhaylychenko, S. S.; Pikun, N. V.; Rusanov, E. B.; Shermolovich, Yu. G. Chem. Heterocycl. Compd. 2015, 51, 128. [Khim. Geterotsikl. Soedin. 2015, 51, 128.]

  3. (a) Kirk, K. L. Org. Process Res. Dev., 2008, 12, 305. (b) Hagmann, W. K. J. Med. Chem. 2008, 51, 4359. (c) Prakash, G. K. S.; Chacko, S. Curr. Opin. Drug Discovery Dev. 2008, 11, 793.

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

    Article  CAS  Google Scholar 

  5. (а) Timoshenko, V. M.; Siry, S. A.; Rozhenko, A. B.; Shermolovich, Yu. G. J. Fluorine Chem. 2010, 131, 172. (b) Siry, S. A.; Timoshenko, V. M. Tetrahedron Lett. 2010, 51, 6406. (c) Mikhailichenko, S. S.; Bouillon, J.-P.; Besson, T.; Shermolovich, Yu. G. Tetrahedron Lett. 2010, 51, 990.

  6. Mloston, G.; Romanski, Ya.; Rusanov, E. B.; Chernega, A. N.; Shermolovich, Yu. G. Zh. Org. Khim. 1995, 31, 1027.

    CAS  Google Scholar 

  7. (a) Padwa, A.; Dent, W. J. Org. Chem. 1987, 52, 235. (b) Planchenault, D.; Wisedale, R.; Gallagher, T.; Hales, N. J. J. Org. Chem. 1997, 62, 3438. (c) Gerbert, A.; Linden, A.; Heimgartner, H. Heterocycles 2001, 54, 691. (d) Gerbert, A.; Linden, A.; Mloston, G.; Heimgartner, H. Polish J. Chem. 2003, 77, 867. (e) Gerbert, A.; Heimgartner, H. Helv. Chim. Acta 2002, 85, 2073. (f) Mloston, G.; Linden, A.; Heimgartner, H. Helv. Chim. Acta 1998, 81, 558.

  8. Mykhaylychenko, S. S.; Bouillon, J.-P.; Shermolovich, Yu. G. J. Fluorine Chem. 2009, 130, 878.

    Article  CAS  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

    Sergiy S. Mykhaylychenko, Serhii A. Siryi, Nadezhda V. Pikun & Yuriy G. Shermolovich

  2. Enamine Ltd, 23 Alexander Matrosov St., Kyiv, 01103, Ukraine

    Sergiy S. Mykhaylychenko

Authors
  1. Sergiy S. Mykhaylychenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Serhii A. Siryi
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Nadezhda V. Pikun
    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(9), 861–864

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Mykhaylychenko, S.S., Siryi, S.A., Pikun, N.V. et al. Synthesis of 5-(polyfluoroalkyl)-1,3-thiazolidines from polyfluoroalkanethiocarboxylic acid derivatives. Chem Heterocycl Comp 51, 861–864 (2015). https://doi.org/10.1007/s10593-015-1787-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-015-1787-1

Keywords

Search

Navigation