Skip to main content
SpringerLink
Log in

Chemical properties of 5-(1,1,2,2-tetrafluoroethoxy)-4-phenylthiazole derivatives

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

In the present study, the possibility of converting [5-(1,1,2,2-tetrafluoroethoxy)-4-phenylthiazol-2-yl]amine to 2-halothiazoles and an azo compound via diazotation of the amine functionality was demonstrated. It was found that the reaction of [5-(1,1,2,2-tetrafluoroethoxy)-4-phenylthiazol-2-yl]amine with acyl and sulfonyl chlorides leads to products resulting from substitution exclusively at the exocyclic nitrogen atom. The halogen atom at position 2 of thiazole ring is substituted by S-nucleophiles or hydrogen atom upon catalytic hydrogenation on Pd/C. 2-Bromo-5-(1,1,2,2-tetrafluoroethoxy)-4-phenylthiazole was successfully employed in the synthesis of the corresponding α-thiazolylbenzyl alcohol and 2-formylthiazole via conversion to a organomagnesium intermediate. The stability of the tetrafluoroethoxy group in the above transformations was demonstrated.

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.

Figure 1
Figure 2
Figure 3

Similar content being viewed by others

References

  1. Wang, J.; Sánchez-Roselló, M.; Acen~a, J. L.; del Pozo, C.; Sorochinsky, A. E.; Fustero, S.; Soloshonok, V. A.; Liu, H. Chem. Rev. 2014, 114, 2432.

    Article  CAS  Google Scholar 

  2. Jimonet, P.; Audiau, F.; Barreau, M.; Blanchard, J.-C.; Boireau, A.; Bour, Y.; Coléno, M.-A.; Doble, A.; Doerflinger, G.; Do Huu, C.; Donat, M.-H.; Duchesne, J. M.; Ganil, P.; Guérémy, C.; Honoré, E.; Just, B.; Kerphirique, R.; Gontier, S.; Hubert, P.; Laduron, P. M.; Le Blevec, J.; Meunier, M.; Miquet, J.-M.; Nemecek, C.; Pasquet, M.; Piot, O.; Pratt, J.; Rataud, J.; Reibaud, M.; Stutzmann, J.-M.; Mignani, S. J. Med. Chem. 1999, 42, 2828.

    Article  CAS  Google Scholar 

  3. Kompendium "Lekarstvenniye preparati"; Kovalenko, V. N.; Viktorova, A. P., Eds.; Morion: Kiev, 2003, p. 666.

  4. Yagupolskii, L. M. Dokl. Akad. Nauk SSSR 1955, 105, 100; Chem. Abstr. 1955, 50, 11270b.

  5. O'Hagan, D. J. Fluorine Chem. 2010, 131, 1071.

    Article  Google Scholar 

  6. Leroux, F.; Jeschke, P.; Schlosser, M. Chem. Rev. 2005, 105, 827.

    Article  CAS  Google Scholar 

  7. Leroux, F. R.; Manteau, B.; Vors, J.-P.; Pazenok, S. Beilstein J. Org. Chem. 2008 , 4, 13.

    Article  Google Scholar 

  8. Hatrz, R. A; Ahuja, V. T.; Zhuo, X.; Mattson, R. J.; Den-hart, D. J.; Deskus, J. A.; Vrudhula, V. M.; Pan, S.; Ditta, J. L.; Shu, Y.-Z.; Grace, J. E.; Lentz, K. A.; Lelas, S.; Li, Y.-W.; Molski, T. F.; Krishnananthan, S.; Wong, H.; Qian-Cutrone, J.; Schartman, R.; Denton, R.; Lodge, N. J.; Zaczek, R.; Macor, J. E.; Bronson, J. J. J. Med. Chem. 2009, 52, 7653.

    Article  Google Scholar 

  9. Mickevičius, V.; Voskienė, A.; Jonuškiene, I.; Kolosej, R.; Šiugždaite, J.; Venskutonis, P. R.; Kazernavičiūtė, R.; Brazienė, Z.; Jakienė, E. Molecules 2013, 18, 15000.

    Article  Google Scholar 

  10. Yagupolskii, L. M.; Nazeretyan, V. P. Ukr. Khim. Zh. 1967, 33, 617; Chem. Abstr. 1967, 67, 91670r.

  11. The Chemistry of Heterocyclic Compounds; Weissberger, A.; Taylor, E. C., Eds., John Wiley & Sons Inc.: New York, 1979, vol. 34, pt. 1–3.

  12. Bartberger, M. D.; Hitchcock, S. A.; Horne, D. B.; Kaller, M. R.; Monenschein, H.; Zhong, W. Tetrahedron Lett. 2009, 50, 5452.

    Article  Google Scholar 

  13. Sokolenko, T. M.; Davydova, Yu. A.; Yagupolskii, Yu. L. J. Fluorine Chem. 2012, 136, 20.

    Article  CAS  Google Scholar 

  14. Weidmann, K.; Herling, A. W.; Lang, H.-J.; Scheunemann, K.-H.; Rippel, R.; Nimmesgern, H.; Scholl, T.; Bickel, M.; Metzger, H. J. Med. Chem. 1992, 35, 438.

    Article  CAS  Google Scholar 

  15. Kohl, B.; Sturm, E.; Senn-Bilfinger, J.; Simon, W. A.; Kruger, U.; Schaefer, H.; Rainer, G.; Figala, V.; Klemm, K. J. Med. Chem. 1992, 35, 1049.

    Article  CAS  Google Scholar 

  16. Yagupolskii, L. M. Aromatic and Heterocyclic Compounds with Fluoro-containing Substitutents [in Russian], Naukova dumka: Kiev, 1988, 283 pp.

    Google Scholar 

  17. Yagupolskii, L. M.; Gandelsman, L. Z. Zh. Obsh. Khim. 1963, 33, 2301; Chem. Abstr. 1964, 60, 692a.

  18. Chattopadhyay, G.; Chakraborty, S.; Saha, C. Synth. Commun. 2008, 38, 4068.

    Article  CAS  Google Scholar 

  19. Kaye, I. A.; Parris, C. L. J. Org. Chem. 1952, 17, 737.

    Article  CAS  Google Scholar 

  20. Dorn, H.; Bedford, G. R.; Hilgetag, G.; Katritzky, A. R. J. Chem. Soc. 1965, 1219.

  21. Liu, Y.; Bai, Y.; Zhang, J.; Li, Y.; Jiao, J.; Qi, X. Eur. J. Org. Chem. 2007, 6084.

  22. Aissaoui, H.; Boss, C.; Hazemann, J.; Koberstein, R.; Siegrist, R.; Sifferlen, T. WO Patent 2010004507.

  23. van Zwieten, P. A.; Huisman, H. O. Recl. Trav. Chim. Pays-Bas 1962, 81, 554.

    Article  Google Scholar 

  24. Gelman, N. E.; Terent'eva, E. A.; Shanina, T. M. Methods of Qualitive Organic Element mikroanalysis, Khimiya: Moscow, 1987, p. 149.

    Google Scholar 

  25. Bekker, H.; Bekkert, R.; Berger, V.; Gevald, K.; Gentz, F.; Gluh, R.; Domshke, G.; Zailer, E.; Mayer, R.; Metz, P.; Muller, K.; Pafel, D.; Fanghenel, E.; Faust, Yu.; Fisher, M.; Habiher, V.; Shvetlik, K.; Shmidt, G.; Sholberg, K.; Zeppenfeld, G. Organikum [in Russian]; Mir: Moscow, 2004, ch. 2, p. 249.

  26. Watkin, D. J.; Prout, C. K.; Carruthers, J. R.; Betteridge, P. W. Crystals; Chemical Crystallography Laboratory, University of Oxford, 1996, Issue 10.

Download references

Author information

Authors and Affiliations

  1. Institute of Organic Chemistry of the NAS of Ukraine, 5 Murmanska St., Kyiv, 02660, Ukraine

    Yulia А. Davydova, Taras M. Sokolenko, Yurii G. Vlasenko & Yurii L. Yagupolskii

Authors
  1. Yulia А. Davydova
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Taras M. Sokolenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Yurii G. Vlasenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Yurii L. Yagupolskii
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Yurii L. Yagupolskii.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2015, 51(1), 80–87

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Davydova, Y.А., Sokolenko, T.M., Vlasenko, Y.G. et al. Chemical properties of 5-(1,1,2,2-tetrafluoroethoxy)-4-phenylthiazole derivatives. Chem Heterocycl Comp 51, 80–87 (2015). https://doi.org/10.1007/s10593-015-1663-z

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-015-1663-z

Keywords

Search

Navigation