Skip to main content
Log in

New heterocyclic derivatives of trifluoroalanine

  • Published:
Russian Journal of General Chemistry Aims and scope Submit manuscript

Abstract

A new method of the synthesis of heterocyclic derivatives of trifluoroalanine based on the cyclocondensation of methyl trifluoropyruvate tert-butoxycarbonylimine with C,N- and N,N-binucleophiles, like Nsubstituted ureas, 1-benzyl-6-aminouracil, benzamidine, and 3-aminocrotononitrile, followed by hydrolysis of the resulting Boc-derivatives to 5-amino-5-trifluoromethylimidazolidine-2,4-diones, 5-amino-5-trifluoromethyl-1-benzyl-5,7-dihydropyrrolo[2,3-d]-pyrimidine-2,4,6-3H-trione, 4-amino-2-methyl-5-oxo-4-(trifluoromethyl)-4,5-dihydro-1H-pyrrole-3-carbonitrile, or 5-amino-5-trifluoromethyl-2-phenyl-3,5-dihydroimidazol-4-one, respectively, was developed.

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. Kukhar, V.P. and Soloshonok, V.A., Fluorine-containing Amino Acids: Synthesis and Properties, Chichester: Wiley, 1995, 422 p.

    Google Scholar 

  2. Biomedical Frontiers of Fluorine Chemistry, Ojima, I., McCarthy, J.R., and Welch, J.T., Eds., Washington: ACS Series 639, 1996, p. 42.

    Google Scholar 

  3. Dal Pozzo, A., Dikovskaya, K., Moroni, M., Fagnoni, M., Vanini, R., Bergonzi, R., de Castiglione, P., Bravo, P., and Zanda, M., J. Chem. Res. (S), 1999, no. 8, p. 468.

    Google Scholar 

  4. Koksch, B., Sewald, N., Hofmann, H.-J., Burger, K., and Jakubke, H.-D., J. Pept. Sci., 1997, vol. 3, no. 3, p. 157.

    Article  CAS  Google Scholar 

  5. Scolnick, L.R., Clements, A.M., Liao, J., Crenshaw, L., Hellberg, M., May, J., Dean, T.R., and Christianson, D.W., J. Am. Chem. Soc., 1997, vol. 119, no. 4, p. 850.

    Article  CAS  Google Scholar 

  6. Sokolov, V.B., Aksinenko, A.Yu., and Martynov, I.V., Russ. Chem. Bull., 2001, no. 6, p. 1113.

    Google Scholar 

  7. Sokolov, V.B., Aksinenko, A.Yu., Goreva, T.V., Epishina, T.A., Pushin, A.N., and Martynov, I.V., Izv. Akad. Nauk, Ser. Khim., 2006, no. 6, p. 1014.

    Google Scholar 

  8. Osipov, S.N., Sokolov, V.B., Kolomiets, A.F., Martynov, I.V., and Fokin, A.V., Russ. Chem. Bull., 1987, no. 5, p. 1098.

    Google Scholar 

  9. Sokolov, V.B., Aksinenko, A.Yu., Epishina, T.A., Goreva, T.V., and Martynov, I.V., Russ. Chem. Bull., 2005, no. 12, p. 2851.

    Google Scholar 

  10. Sokolov, V.B., Aksinenko, A.Yu., Epishina, T.A., Goreva, T.V., and Martynov, I.V., Russ. Chem. Bull., 2005, no. 2, p. 470.

    Google Scholar 

  11. Sokolov, V.B., Aksinenko, A.Yu., and Martynov, I.V., Russ. Chem. Bull., 2005, no. 6, p. 1514.

    Google Scholar 

  12. Sokolov, V.B., Aksinenko, A.Yu., and Martynov, I.V., Russ. Chem. Bull., 2007, no. 11, p. 2247.

    Google Scholar 

  13. Osipov, S.N., Shchetnikov, G.T., Zotova, M.A., Bruneau, C., and Dixneuf, P.H., Eur. J. Org. Chem., 2010, no. 8, p. 1587.

    Google Scholar 

  14. Osipov, S.N., Peregudov, A.S., and Shchetnikov, G.T., Synlett, 2007, no. 1, p. 136.

    Google Scholar 

  15. Bolm, C., Husmann, R., Mersmann, S., Raabe, G., Rueping, M., and Sugiono, E., Org. Lett., 2011, vol. 13, no. 5, p. 1044.

    Article  Google Scholar 

  16. Sokolov, V.B. and Aksinenko, A.Yu., Russ. Chem. Bull., 1998, no. 4, p. 727.

    Google Scholar 

  17. Hatzenlaub, W. and Pfleiderer, W., Lieb. Ann. Chem., 1979, no. 11, p. 1847.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to A. Yu. Aksinenko.

Additional information

Original Russian Text © V.B. Sokolov, A.Yu. Aksinenko, T.A. Epishina, T.V. Goreva, 2014, published in Zhurnal Obshchei Khimii, 2014, Vol. 84, No. 7, pp. 1163–1166.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Sokolov, V.B., Aksinenko, A.Y., Epishina, T.A. et al. New heterocyclic derivatives of trifluoroalanine. Russ J Gen Chem 84, 1358–1361 (2014). https://doi.org/10.1134/S1070363214070184

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363214070184

Keywords

Navigation