Russian Chemical Bulletin

, Volume 65, Issue 2, pp 473–478 | Cite as

Novel route of the reaction of trifluoromethyl-containing N-methyl(4-ethoxyphenyl)imidazolidin-2-ones with urea

  • L. V. Saloutina
  • A. Ya. Zapevalov
  • P. A. Slepukhin
  • M. I. Kodess
  • V. I. Saloutin
  • O. N. Chupakhin
Full Articles


The reactions of perfluorobiacetyl with N-(4-ethoxyphenyl)- and N-methylurea afforded cis- and trans-isomers of 1-methyl-4,5-dihydroxy-4,5-bis(trifluoromethyl)imidazolidin-2-one and 1-(4-ethoxyphenyl)-4,5-dihydroxy-4,5-bis(trifluoromethyl)imidazolidin-2-one in a yield of ∼60—75%. N-Alkyl(aryl)bis(trifluoromethyl)imidazooxazoles were obtained as unexpected products in the reaction of 1-alkyl(aryl)-4,5-dihydroxy-4,5-bis(trifluoromethyl)imidazolidin-2-ones with urea in dimethylacetamide. The reaction is accompanied by the rearrangement of imidazolidin-2-ones to N-alkyl(aryl)-5,5-bis(trifluoromethyl)hydantoins with CF3 group migration from position 5 to position 4 of the starting heterocycle. A similar rearrangement is observed on boiling of the studied imidazolidin-2-ones in dimethylacetamide. The molecular structures of 3-(4-ethoxyphenyl)-5,5-bis(trifluoromethyl)imidazolidine-2,4-dione and 6-(4-ethoxyphenyl)-3a,6a-bis(trifluoromethyl)tetrahydroimidazo[4,5-d]oxazole-2,5-dione were studied by X-ray diffraction analysis.

Key words

perfluorobiacetyl N-(4-ethoxyphenyl)urea N-methylurea urea 4,5-dihydroxy-4,5-bis(trifluoromethyl)imidazolidin-2-ones cis- and trans-isomers imidazooxazoles hydantoins X-ray diffraction analysis 


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  1. 1.
    M. D. Mashkovskii, Lekarstvennye sredstva [Drugs], Novaya Volna, Moscow, 2002, Vol. 1, 39; 86 (in Russian).Google Scholar
  2. 2.
    D. Ajami, J. Rebek, Jr, J. Am. Chem. Soc., 2006, 128, 5314.CrossRefGoogle Scholar
  3. 3.
    Pat. DE 3530666; Chem. Abstr., 1987, 107, 41059.Google Scholar
  4. 4.
    A. N. Kravchenko, A. S. Sigachev, E. Yu. Maksareva, G. A. Gazieva, N. S. Trunova, B. V. Lozhkin, T. S. Pivina, M. M. Il´in, K. A. Lyssenko, Yu. V. Nelyubina, V. A. Davankov, O. V. Lebedev, N. N. Makhova, V. A. Tartakovskii, Russ. Chem. Bull. (Int. Ed.), 2005, 54, 691 [Izv. Akad. Nauk, Ser. Khim., 2005, 680].CrossRefGoogle Scholar
  5. 5.
    Pat. DE 4303522; Chem. Abstr., 1994, 121, 205400.Google Scholar
  6. 6.
    N. She, M. Gao, L. Cao, G. Yin, A. Wu, Synlett, 2007, 18, 2533.Google Scholar
  7. 7.
    M. Kölbel, F. M. Menger, Adv. Mater., 2001, 13, 1115.CrossRefGoogle Scholar
  8. 8.
    Eur. Pat 437784; Chem. Abstr., 1991, 115, 232244.Google Scholar
  9. 9.
    L. V. Saloutina, A. Ya. Zapevalov, V. I. Saloutin, P. A. Slepukhin, M. I. Kodess, O. N. Chupakhin, J. Fluorine Chem., 2009, 130, 853.CrossRefGoogle Scholar
  10. 10.
    L. V. Saloutina, A. Ya. Zapevalov, P. A. Slepukhin, M. I. Kodess, V. I. Saloutin, O. N. Chupakhin, Chem. Heterocycl. Compd. (Engl. Transl.), 2014, 50, 958 [Khim. Geterotsikl. Soedinen., 2014, 50, 1040].CrossRefGoogle Scholar
  11. 11.
    L. V. Saloutina, A. Ya. Zapevalov, M. I. Kodess, V. I. Saloutin, O. N. Chupakhin, Mendeleev Commun., 1999, 231.Google Scholar
  12. 12.
    S. L. Vail, R. H. Barket, P. G. Mennitt, J. Org. Chem., 1965, 30, 2179.CrossRefGoogle Scholar
  13. 13.
    R. J. Nachman, J. Heterocycl. Chem., 1983, 20, 1423.CrossRefGoogle Scholar
  14. 14.
    W. R. Dunnavant, F. L. James, J. Am. Chem. Soc., 1956, 78, 2740.CrossRefGoogle Scholar
  15. 15.
    G. A. Gazieva, P. V. Lozhkin, V. V. Baranov, Yu. V. Nelyubina, A. N. Kravchenko, N. N. Makhova, Russ. Chem. Bull. (Int. Ed.), 2009, 58, 2488 [Izv. Akad. Nauk, Ser. Khim., 2009, 2408].CrossRefGoogle Scholar
  16. 16.
    V. Wehner, H.-U. Stils, S. N. Osipov, A. S. Golubev, J. Sieler, K. Burger, Tetrahedron, 2004, 60, 4295.CrossRefGoogle Scholar
  17. 17.
    C. G. Krespan, B. E. Smart, E. G. Howard, J. Am. Chem. Soc., 1977, 99, 1214.CrossRefGoogle Scholar
  18. 18.
    G. M. Sheldrick, Acta Crystallogr., Sect. A, 2008, 64, 112.CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2016

Authors and Affiliations

  • L. V. Saloutina
    • 1
  • A. Ya. Zapevalov
    • 1
  • P. A. Slepukhin
    • 1
  • M. I. Kodess
    • 1
  • V. I. Saloutin
    • 1
  • O. N. Chupakhin
    • 1
  1. 1.I. Ya. Postovsky Institute of Organic SynthesisUral Branch of the Russian Academy of SciencesYekaterinburgRussian Federation

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