Chemistry of Heterocyclic Compounds

, Volume 51, Issue 9, pp 838–844 | Cite as

Synthesis and reactivity of 8-aza-5,7-dimethyl-2-trifluoroacetylchromone

  • Alexander V. Safrygin
  • Mikhail A. Barabanov
  • Roman A. Irgashev
  • Vyacheslav Ya. Sosnovskikh

Claisen condensation of 3-acetyl-4,6-dimethyl-2-pyridone with methyl 2-methoxytetrafluoropropionate in the presence of LiH in refluxing dioxane gave the corresponding 1,3-diketone, further converted by treatment with conc. H2SO4 to 5,7-dimethyl-2-(1-methoxytetrafluoroethyl)-8-azachromone and 5,7-dimethyl-2-trifluoroacetyl-8-azachromone, which was isolated as hydrate. The first of these azachromones reacted with dinucleophiles at the С-2 atom and the pyrone carbonyl group, while the second reacted at the С-2 atom and trifluoroacetyl group. Based on these compounds, we obtained new trifluoromethylated heterocyclic systems containing a 2-pyridone ring, as well as (8-azachromon-2-yl)(indol-3-yl)carbinols.


8-azachromones bis-hetarylcarbinols 1,2-diamines indoles quinoxalines trifluoromethylated heterocycles 


  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) Ji, Y.; Brueckl, T.; Baxter, R. D.; Fujiwara, Y.; Seiple, I. B.; Su, S.; Blackmond, D. G.; Baran, P. S. Proc. Natl. Acad. Sci. U. S. A. 2011, 108, 14411. (b) Fujiwara, Y.; Dixon, J. A.; Rodriguez, R. A.; Baxter, R. D.; Dixon, D. D.; Collins, M. R.; Blackmond, D. G.; Baran, P. S. J. Am. Chem. Soc. 2012, 134, 1494. (c) Kino, T.; Nagase, Y.; Ohtsuka, Y.; Yamamoto, K.; Uraguchi, D.; Tokuhisa, K.; Yamakawa, T. J. Fluorine Chem. 2010, 131, 98.Google Scholar
  3. 3.
    (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. (e) Isakova, V. G.; Khlebnikova, T. S.; Lakhvich, F. A. Russ. Chem. Rev. 2010, 79, 849. (f) Korotaev, V. Y.; Sosnovskikh, V. Y.; Barkov, A. Y. Russ. Chem. Rev. 2013, 82, 1081.Google Scholar
  4. 4.
    (a) Sosnovskikh, V. Y. In Fluorine in Heterocyclic Chemistry; Nenajdenko, V., Ed.; Springer: Cham, Heidelberg, New York, Dordrecht, London, 2014, Vol. 2, p. 211.Google Scholar
  5. 5.
    (a) Irgashev, R. A.; Sosnovskikh, V. Y.; Kalinovich, N.; Kazakova, O.; Röschenthaler, G.-V. Tetrahedron Lett. 2009, 50, 4903. (b) Irgashev, R. A.; Safrygin, A. V.; Ezhikova, M. A.; Kodess, M. I.; Röschenthaler, G.-V.; Sosnovskikh, V. Y. Tetrahedron 2015, 71, 1822.Google Scholar
  6. 6.
    (a) Sosnovskikh, V. Y.; Irgashev, R. A.; Barabanov, M. A. Synthesis 2006, 2707. (b) Sosnovskikh, V. Y.; Usachev, B. I.; Sizov, A. Y.; Barabanov, M. A. Synthesis 2004, 942. (c) Sosnovskikh, V. Y.; Barabanov, M. A.; Usachev, B. I. Russ. Chem. Bull., Int. Ed. 2003, 52, 1758. [Izv. Akad. Nauk, Ser. Khim. 2003, 1668.]Google Scholar
  7. 7.
    (a) Sianesi, D.; Pasetti, A.; Tarli, F. J. Org. Chem. 1966, 31, 2312. (b) Dolenský, B.; Kvíčala, J.; Paleček, J.; Paleta, O. J. Fluorine Chem. 2002, 115, 67.Google Scholar
  8. 8.
    Cushman, M.; Patel, H.; McKenzie, A. J. Org. Chem. 1988, 53, 5088.CrossRefGoogle Scholar
  9. 9.
    (a) Horton, D. A.; Bourne, G. T.; Smythe, M. L. Chem. Rev. 2003, 103, 893. (b) Golantsov, N. E.; Festa, A. A.; Karchava, A. V.; Yurovskaya, M. A. Chem. Heterocycl. Compd. 2013, 49, 203. [Khim. Geterotsikl. Soedin. 2013, 224.] (c) Gupta, N.; Goyal, D. Chem. Heterocycl. Compd. 2015, 51, 4. [Khim. Geterotsikl. Soedin. 2015, 51, 4.]Google Scholar
  10. 10.
    Morales-Ríos, M. S.; Joseph-Nathan, P. Magn. Res. Chem. 1987, 25, 911.CrossRefGoogle Scholar
  11. 11.
    Bonsall, C.; Hill, J. J. Chem. Soc. C 1967, 1836.Google Scholar

Copyright information

© Springer Science+Business Media New York 2015

Authors and Affiliations

  • Alexander V. Safrygin
    • 1
  • Mikhail A. Barabanov
    • 1
  • Roman A. Irgashev
    • 1
    • 2
  • Vyacheslav Ya. Sosnovskikh
    • 1
  1. 1.Institute of Natural SciencesUral Federal University named after the First President of Russia B. N. YeltsinYekaterinburgRussia
  2. 2.I. Ya. Postovskii Institute of Organic SynthesisUral Branch of the Russian Academy of SciencesYekaterinburgRussia

Personalised recommendations