Advertisement

Russian Journal of Organic Chemistry

, Volume 52, Issue 4, pp 533–537 | Cite as

Reaction of 1-[2-(vinyloxy)ethyl]-1H-pyrroles with trifluoroacetic anhydride

  • E. Kh. Sadykov
  • N. A. Lobanova
  • V. K. Stankevich
Review
  • 37 Downloads

Abstract

Chemo- and stereoselectivity of the reaction of 1-[2-(vinyloxy)ethyl]-1H-pyrroles with trifluoroacetic anhydride have been studied. The reaction with an equimolar amount of trifluoroacetic anhydride chemoselectively involves the free α-position of the pyrrole ring with formation of the corresponding α-trifluoroacetylpyrroles. In the reaction with 2 equiv of trifluoroacetic anhydride, acylation of both α-position of the pyrrole ring and β-position of the vinyloxy group leads to the formation of 1-(2-{[(1E)-4,4,4-trifluoro-3-oxobut-1-en-1-yl]oxy}ethyl)-2-trifluoroacetyl derivatives with high stereoselectivity.

Keywords

Pyrrole Vinyl Ether Pyrrole Ring Trifluoroacetyl Trifluoroacetic Anhydride 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Purser, S., Moore, P.R., Swallow, S., and Gouverneur, V., Chem. Soc. Rev., 2008, vol. 37, p. 320.CrossRefGoogle Scholar
  2. 2.
    Giornal, F., Pazenok, S., Rodefeld, L., Lui, N., Vors, J.-P., and Leroux, F.R., J. Fluorine Chem., 2013, vol. 152, p. 2.CrossRefGoogle Scholar
  3. 3.
    Kirsch, P., Modern Fluoroorganic Chemistry: Synthesis, Reactivity, Applications, Weinheim: Wiley-VCH, 2013, 2nd ed., p. 245.CrossRefGoogle Scholar
  4. 4.
    Wang, J., Sánchez-Roselló, M., Aceña, J.L., del Pozo, C., Sorochinsky, A.E., Fustero, S., Soloshonok, V.A., and Liu, H., Chem. Rev., 2014, vol. 114, p. 2432.CrossRefGoogle Scholar
  5. 5.
    Bassetto, M., Ferla, S., and Pertusati, F., Future Med. Chem., 2015, vol. 7, p. 527.CrossRefGoogle Scholar
  6. 6.
    Müller, K., Faeh, C., and Diederich, F., Science, 2007, vol. 317, p. 1881.CrossRefGoogle Scholar
  7. 7.
    Zhu, W., Wang, J., Wang, S., Gu, Z., Aceña, J.L., Izawa, K., Liu, H., and Soloshonok, V.A., J. Fluorine Chem., 2014, vol. 167, p. 37.CrossRefGoogle Scholar
  8. 8.
    Nenajdenko, V., Muzalevskiy, V., and Serdyuk, O., Fluorine in Heterocyclic Chemistry, Nenajdenko, V, Ed., Heidelberg: Springer, 2014, vol. 1, p. 55.Google Scholar
  9. 9.
    Clementi, S. and Marino, G., Tetrahedron, 1969, vol. 25, p. 4599.CrossRefGoogle Scholar
  10. 10.
    Clementi, S. and Marino, G.J., Chem. Soc., Perkin Trans. 2, 1972, p. 71.Google Scholar
  11. 11.
    Yarmoliuk, D.V., Arkhipov, V.V., Stambirskyi, M.V., Dmytriv, Y.V., Shishkin, O.V., Tolmachev, A.A., and Mykhailiuk, P.K., Synthesis, 2014, vol. 46, p. 1254.CrossRefGoogle Scholar
  12. 12.
    Nenajdenko, V.G. and Balenkova, E.S., Arkivoc, 2011, part (i), p. 246.Google Scholar
  13. 13.
    Trofimov, B.A., Schmidt, E.Yu., and Sobenina, L.N., Chemistry of Pyrroles, Boca Raton, FL: CRC, 2014, p. 272.Google Scholar
  14. 14.
    Anderson, H.J. and Loader, C.E., Pyrroles. Part One: The Synthesis and the Physical and Chemical Aspects of the Pyrrole Ring, Jones, R.A., Ed., Hoboken, NJ: Wiley, 1990, p. 398.Google Scholar
  15. 15.
    Hojo, M., Masuda, R., Kokuryo, Y., Shioda, H., and Matsuo, S., Chem. Lett., 1976, vol. 5, p. 499.CrossRefGoogle Scholar
  16. 16.
    Hojo, M., Masuda, R., and Okada, E., Synthesis, 1990, no. 4, p. 347.CrossRefGoogle Scholar
  17. 17.
    Kelly, C.B., Mercadante, M.A., and Leadbeater, N.E., Chem. Commun., 2013, vol.49, p. 11 133.CrossRefGoogle Scholar
  18. 18.
    Abdel-Aal, Y. and Hammock, B., Science, 1986, vol. 233, p. 1073.CrossRefGoogle Scholar
  19. 19.
    Sadykov, E.K., Lobanova, N.A., and Stankevich, V.K., Synthesis, 2015, vol. 47, p. 67.Google Scholar

Copyright information

© Pleiades Publishing, Ltd. 2016

Authors and Affiliations

  • E. Kh. Sadykov
    • 1
  • N. A. Lobanova
    • 1
  • V. K. Stankevich
    • 1
  1. 1.Favorskii Irkutsk Institute of Chemistry, Siberian BranchRussian Academy of SciencesIrkutskRussia

Personalised recommendations