Advertisement

Chemistry of Heterocyclic Compounds

, Volume 53, Issue 12, pp 1362–1364 | Cite as

Reactions of 2-(trifluoroacetyl)chromones with aromatic amines

  • Alexander V. Safrygin
  • Darya A. Vetyugova
  • Roman A. Irgashev
  • Vyacheslav Ya. SosnovskikhEmail author
SHORT COMMUNICATIONS

Aromatic amines reacted with 2-(trifluoroacetyl)chromones as С- or N-nucleophiles, depending on the conditions. When the reaction was performed under solvent-free conditions at 100°С for 12–18 h, they acted as С-nucleophiles and gave bishetarylcarbinols in 21–67% yields, while in refluxing toluene the addition of primary arylamines occurred via the amino group, providing the corresponding hemiaminals (80–86%).

Keywords

anilines bishetarylcarbinols hemiaminals 2-(trifluoroacetyl)chromones 

Notes

This work received financial support from the Russian Foundation for Basic Research (grant No. 17-03-00340).

References

  1. 1.
    (a) Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications; Filler, R.; Kobayashi, Y.; Yagupolskii, L. M., Eds.; Elsevier: Amsterdam, 1993. (b) Hiyama, T. Organofluorine Compounds: Chemistry and Application; Springer: Berlin, 2000. (c) Kirk, K. L. J. Fluorine Chem. 2006, 127, 1013. (d) Bégué, J.-P.; Bonnet-Delpon, D. J. Fluorine Chem. 2006, 127, 992. (e) Dolbier, W. R., Jr. J. Fluorine Chem. 2005, 126, 157.Google Scholar
  2. 2.
    (a) Lin, P.; Jiang, J. Tetrahedron 2000, 56, 3635. (b) Druzhinin, S. V.; Balenkova, E. S.; Nenajdenko, V. G. Tetrahedron 2007, 63, 7753. (c) Nenajdenko, V. G.; Balenkova, E. S. ARKIVOC 2011, (i), 246. (d) Sosnovskikh, V. Y. Russ. Chem. Rev. 2003, 72, 489. [Usp. Khim. 2003, 72, 550.] (e) Isakova, V. G.; Khlebnikova, T. S.; Lakhvich, F. A. Russ. Chem. Rev. 2010, 79, 849. [Usp. Khim. 2010, 79, 929.] (f) Korotaev, V. Y.; Sosnovskikh, V. Y.; Barkov, A. Y. Russ. Chem. Rev. 2013, 82, 1081. [Usp. Khim. 2013, 82, 1081.]Google Scholar
  3. 3.
    Sosnovskikh, V. Y. In Fluorine in Heterocyclic Chemistry; Nenajdenko, V., Ed.; Springer: Cham, 2014, Vol. 2, p. 211.CrossRefGoogle Scholar
  4. 4.
    Irgashev, R. A.; Safrygin, A. V.; Ezhikova, M. A.; Kodess, M. I.; Röschenthaler, G.-V.; Sosnovskikh, V. Y. Tetrahedron 2015, 71, 1822.CrossRefGoogle Scholar
  5. 5.
    Safrygin, A. V.; Irgashev, R. A.; Barabanov, M. A.; Sosnovskikh, V. Y. Tetrahedron 2016, 72, 227.CrossRefGoogle Scholar
  6. 6.
    (a) Khodakovskiy, P. V.; Mykhailiuk, P. K.; Volochnyuk, D. M.; Tolmachev, A. A. Synthesis 2010, 967. (b) Khodakovskiy, P. V.; Mykhailiuk, P. K.; Volochnyuk, D. M.; Tolmachev, A. A. Synthesis 2010, 979. (c) Khodakovskiy, P. V.; Mykhailiuk, P. K.; Volochnyuk, D. M.; Tolmachev, A. A. Synthesis 2010, 1195.Google Scholar
  7. 7.
    Khodakovskiy, P. V.; Mykhailiuk, P. K.; Volochnyuk, D. M.; Tolmachev, A. A. Synthesis 2010, 1633.Google Scholar

Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  • Alexander V. Safrygin
    • 1
  • Darya A. Vetyugova
    • 1
  • Roman A. Irgashev
    • 1
    • 2
  • Vyacheslav Ya. Sosnovskikh
    • 1
    Email author
  1. 1.Institute of Natural Sciences and MathematicsUral Federal University named after the first President of Russia B. N. YeltsinYekaterinburgRussia
  2. 2.Postovsky Institute of Organic SynthesisUral Branch of the Russian Academy of SciencesYekaterinburgRussia

Personalised recommendations