Skip to main content
SpringerLink
Log in

Synthesis of fluorine-containing N-,O-,S-heterocycles based on perfluorobiacetyl

  • Reviews
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

The review presents approaches to the synthesis of trifluoromethyl-containing N,O,S-heterocyclic compounds such as imidazolidin-2-ones(thiones), 1,2,4-triazine-3-thiones(ones), 1,2,4-triazine-3-amines, bis(trifluoromethyl)-2,3-dihydropyrazine-1,4-dioxides based on reactions of perfluorobiacetyl with bi- and trifunctional nucleophilic agents: urea, N- and N,N′-substituted ureas, thiourea, thiosemicarbazide, semicarbazide hydrochloride, aminoguanidine bicarbonate, and N,N′-dihydroxy-2,3-dimethylbutane-2,3-diamine. The reaction of 4,5-dihydroxy-4,5-bis(trifluoromethyl)imidazilidin-2-one with urea in N,N-dimethylacetamide at elevated temperature afforded bis(trifluoromethyl)-glycoluril. Monosubstituted N-alkyl(aryl)-4,5-dihydroxy-4,5-bis(trifluoromethyl)imidazolidin-2-ones reacted with urea under similar conditions to give 1-alkyl(aryl)bis(trifluoromethyl)imidazooxazoles. The condensation reaction of trifluoromethyl-containing imidazolidin-2-ones(thiones) with thiourea and NH4SCN in a dipolar aprotic solvent at elevated temperature resulted in thioglycolurils, thioxoimidazothiazolones, and oxoimidazothiazolones. The first nitrogen-containing heterocycles containing a CF3 group at the vicinal position to the N-O fragment were synthesized by the reaction of perfluorobiacetyl with N,N′-dihydroxy-2,3-dimethylbutane-2,3-diamine.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

References

  1. C. G. Krespan, B. E. Smart, E. G. Howard, J. Am. Chem. Soc., 1977, 99, 1214; DOI: https://doi.org/10.1021/ja00446a037.

    Article  CAS  Google Scholar 

  2. V. I. Saloutin, K. I. Pashkevich, I. Ya. Postovskii, Russ. Chem. Rev., 1982, 51, 736; DOI: https://doi.org/10.1070/RC1982v051n08ABEH002904.

    Article  Google Scholar 

  3. M. Cushman, W. Ch. Wong, A. Bacher, J. Chem. Soc., Perkin Trans. 1, 1986, 1043; DOI: https://doi.org/10.1039/P19860001043.

  4. M. Cushman, W. Ch. Wong, A. Bacher, J. Chem. Soc., Perkin Trans. 1, 1986, 1051; DOI: https://doi.org/10.1039/P19860001051.

  5. A. N. Kravchenko, V. V. Baranov, G. A. Gazieva, Russ. Chem. Rev., 2018, 87, 89; DOI: https://doi.org/10.1070/RCR4763.

    Article  CAS  Google Scholar 

  6. M. D. Mashkovsky, Lekarstvennye sredstva [Medicines], Novaya volna, Moscow, 2002, V. 1, p. 39, 86 (in Russian).

    Google Scholar 

  7. S. S. Novikov, Bull. Acad. Sci. USSR, Div. Chem. Sci., 1979, 28, 2083; DOI: https://doi.org/10.1007/BF00947558.

    Article  Google Scholar 

  8. A. O. Kuptsova, E. E. Vinogradova, A. N. Kravchenko, G. A. Gazieva, Russ. Chem. Bull., 2022, 71, 885; DOI: https://doi.org/10.1007/s11172-022-3488-0.

    Article  CAS  Google Scholar 

  9. D. Ajami, J. Rebek, Jr., J. Am. Chem. Soc., 2006, 128, 5314; DOI: https://doi.org/10.1021/ja060095q.

    Article  CAS  PubMed  Google Scholar 

  10. DE Pat. 3530666; Chem. Abstr., 1987, 107, 41059x.

  11. DE Pat. 4303522; Chem. Abstr., 1994, 121, 205400n.

  12. N. She, M. Gao, L. Cao, G. Yin, A. Wu, Synlett, 2007, 18, 2533; DOI: https://doi.org/10.1055/s-2007-986671.

    Google Scholar 

  13. S. Y. Panshina, O. V. Ponomarenko, A. A. Bakibaev, V. S. Sidelnikov, D. A. Kurgachev, V. S. Malkov, A. I. Khlebnikov, A. K. Tashenov, Russ. Chem. Bull., 2021, 70, 140; DOI: https://doi.org/10.1007/s11172-021-3068-8.

    Article  CAS  Google Scholar 

  14. M. Kölbel, F. M. Menger, Adv. Mater., 2001, 13, 1115; DOI: https://doi.org/10.1002/1521-4095(200107)13:14<1115::AID-ADMA1115>3.0.CO;2-Y.

    Article  Google Scholar 

  15. Eur. Pat 437784; Chem. Abstr., 1991, 115, 232244.

  16. Ru. Pat. 2150469; Chem. Abstr., 2002, 136, 247485.

  17. L. V. Saloutina, A. Ya. Zapevalov, P. A. Slepukhin, M. I. Kodess, V. I. Saloutin, O. N. Chupakhin, Chem. Heterocycl. Compd., 2014, 50, 958; DOI: https://doi.org/10.1007/s10593-014-1550-z.

    Article  CAS  Google Scholar 

  18. L. V. Saloutina, A. Ya. Zapevalov, P. A. Slepukhin, M. I. Kodess, V. I. Saloutin, O. N. Chupakhin, Russ. Chem. Bull., 2016, 65, 473; DOI: https://doi.org/10.1007/s11172-016-1324-0.

    Article  CAS  Google Scholar 

  19. L. V. Saloutina, A. Ya. Zapevalov, M. I. Kodess, P. A. Slepukhin, I. N. Ganebnykh, V. I. Saloutin, O. N. Chupakhin, AIP Conf. Proc., 2022, 2390, 020069; DOI: https://doi.org/10.1063/5.0069424.

    Article  CAS  Google Scholar 

  20. V. V. Baranov, G. A. Gazieva, Yu. V. Nelyubina, A. N. Kravchenko, N. N. Makhova, Russ. J. Org. Chem., 2011, 47, 1564; DOI: https://doi.org/10.1134/S1070428011100204.

    Article  CAS  Google Scholar 

  21. V. V. Baranov, A. N. Kravchenko, Yu. V. Nelyubina, Mendeleev Commun., 2014, 24, 105; DOI: https://doi.org/10.1016/j.mencom.2014.03.014.

    Article  CAS  Google Scholar 

  22. V. V. Baranov, Yu. V. Nelyubina, A. N. Kravchenko, N. G. Kolotyrkina, K. A. Biriukova, Tetrahedron Lett., 2015, 56, 6085; DOI: https://doi.org/10.1016/j.tetlet.2015.09.071.

    Article  CAS  Google Scholar 

  23. A. N. Kravchenko, M. M. Antonova, V. V. Baranov, Yu. V. Nelyubina, Synlett, 2015, 26, 2521; DOI: https://doi.org/10.1055/s-0035-1560657.

    Article  CAS  Google Scholar 

  24. V. V. Baranov, M. M. Antonova, V. A. Karnoukhova, A. N. Kravchenko, ARKIVOC, 2017, Part iii, 63; DOI: https://doi.org/10.3998/ark.5550190.p010.048.

  25. G. A. Gazieva, V. V. Baranov, A. N. Kravchenko, N. N. Makhova, Russ. J. Org. Chem., 2011, 47, 1572; DOI: https://doi.org/10.1134/s1070428011100216.

    Article  CAS  Google Scholar 

  26. G. A. Gazieva, Yu. B. Vikharev, L. V. Anikina, T. B. Karpova, A. N. Kravchenko, E. A. Permyakov, I. V. Svitanko, Mendeleev Commun., 2013, 23, 202; DOI: j.mencom.2013.07.007.

    Article  CAS  Google Scholar 

  27. G. A. Gazieva, L. V. Anikina, T. V. Nechaeva, S. A. Pukhov, T. V. Karpova, S. V. Popkov, Yu. V. Nelyubina, N. G. Kolotyrkina, A. N. Kravchenko, Eur. J. Med. Chem., 2017, 140, 141; DOI: https://doi.org/10.1016/j.ejmech.2017.09.009.

    Article  CAS  PubMed  Google Scholar 

  28. G. G. Muccoli, N. Fasio, G. K. E. Scriba, W. Poppitz, F. Cannata, J. H. Poupaert, J. Wouters, D. M. Lambert, J. Med. Chem., 2006, 49, 417; DOI: 10.102/jm050977k.

    Article  Google Scholar 

  29. L. V. Saloutina, A. Ya. Zapevalov, M. I. Kodess, I. N. Ganebnykh, V. I. Saloutin, O. N. Chupakhin, J. Fluorine Chem., 2018, 212, 144; DOI: https://doi.org/10.1016/J.JFLUCHEM.2018.05.015.

    Article  CAS  Google Scholar 

  30. A. M. Golub, H. Köhler, V. V. Skopenko, Chemie der Pseudohalogenide, 1979, Deutscher Verl. der Wiss., Berlin, 440 S.

    Google Scholar 

  31. G. H. Buchanan, The Cyanogen Compounds, in Allen’s Commercial Organic Analysis, Vol. 8, P. Blakiston’s Son &Co. Publ., Philadelphia, 1930.

    Google Scholar 

  32. A. R. Katritsky, A. F. Pozharskii, Handbook of Heterocyclic Chemistry, Pergamon, Oxford, 2000, p. 596.

    Google Scholar 

  33. US Pat. 3979516; Chem. Abstr., 1977, 86, 72707j.

  34. W. M. Al-Adiwish, M. I. M. Tahir, A. Siti-Noor-Adnalizawati, S. F. Hashim, N. Ibrahim, W. A. Yaacob, Eur. J. Med. Chem., 2013, 64, 464; DOI: https://doi.org/10.1016/j.ejmech.2013.04.029.

    Article  CAS  PubMed  Google Scholar 

  35. K. Wasti, M. M. Joullie, Heterocyeles, 1976, 4, 1341; DOI: https://doi.org/10.3987/R-1986-08-341.

    Article  CAS  Google Scholar 

  36. K. Sztanke, K. Pasternak, B. Rajtar, M. Sztanke, M. Majek, M. Polz-Dacewicz, Bioorg. Med. Chem., 2007, 15, 5480; DOI: https://doi.org/10.1016/j.bmc.2007.05.048.

    Article  CAS  PubMed  Google Scholar 

  37. V. L. Rusinov, V. N. Charushin, O. N. Chupakhin, Russ. Chem. Bull., 2018, 67, 573; DOI: https://doi.org/10.1007/s11172-018-2113-8.

    Article  CAS  Google Scholar 

  38. P. N. Tripathi, P. Srivastava, P. Sharma, M. K. Tripathi, A. Seth, A. Tripathi, S. N. Rai, S. P. Singh, S. K. Shrivastava, Bioorg. Chem., 2019, 85, 82; DOI: https://doi.org/10.1016/j.bioorg.2018.12.017.

    Article  CAS  PubMed  Google Scholar 

  39. S. S. Smagin, V. E. Bogachev, A. K. Yakubovskii, S. E. Metlakova, T. P. Privol’eva, V. V. Chugunov, E. F. Lavretskaya, J. Pharm. Chem., 1975, 9, 222; DOI: https://doi.org/10.1007/BF00758880.

    Article  Google Scholar 

  40. M. Mizutani, R. Yoshida, Y. Sanemitsu, Agric. Biol. Chem., 1987, 51, 3177; DOI: https://doi.org/10.1271/bbb1961.51.3177.

    CAS  Google Scholar 

  41. M. M. Ganiev, V. D. Nedorezkov, Khimicheskie sredstva zashchity rasteniy [Chemical Agents of Plant Protection], KolosS, Moscow, 2006, 248 pp. (in Russian).

    Google Scholar 

  42. Ru. Pat. 2146251; Chem. Abstr., 2001, 135, 272992r (in Russian).

  43. Ru. Pat. 2146252; Chem. Abstr., 2001, 135, 272993s (in Russian).

  44. L. V. Saloutina, A. Ya. Zapevalov, M. I. Kodess, P. A. Slepukhin, I. N. Ganebnykh, V. I. Saloutin, O. N. Chupakhin, J. Fluorine Chem., 2019, 227, 109362; DOI: https://doi.org/10.1016/j.jfluchem.2019.109362.

    Article  CAS  Google Scholar 

  45. E. E. Reid, Organic Chemistry of Bivalent Sulfur, Chemical Publishing Co., New York, 1963, v. 5, p. 197.

    Google Scholar 

  46. Ru. Pat. 2235088; Chem. Abstr., 2001, 134, 115676c (in Russian).

  47. L. V. Saloutina, E. V. Tretyakov, P. A. Slepukhin, V. I. Saloutin, O. N. Chupakhin, J. Heterocycl. Chem., 2017, 54, 1887; DOI: https://doi.org/10.1002/J.het.2782.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22 ul. S. Kovalevskoi/20 Akademicheskaya, 620108, Ekaterinburg, Russian Federation

    L. V. Saloutina, V. I. Saloutin & O. N. Chupakhin

  2. Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 ul. Mira, 620002, Ekaterinburg, Russian Federation

    V. I. Saloutin & O. N. Chupakhin

Authors
  1. L. V. Saloutina
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. V. I. Saloutin
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. O. N. Chupakhin
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to L. V. Saloutina.

Ethics declarations

The authors declare no competing interests.

Additional information

This work was financially supported by the Ministry of Science and Higher Education of the Russian Federation (Project AAAA-A19-119011790132-7).

No human or animal subjects were used in this research.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 72, No. 8, pp. 1725–1736, August, 2023.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Saloutina, L.V., Saloutin, V.I. & Chupakhin, O.N. Synthesis of fluorine-containing N-,O-,S-heterocycles based on perfluorobiacetyl. Russ Chem Bull 72, 1725–1736 (2023). https://doi.org/10.1007/s11172-023-3954-3

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-023-3954-3

Keywords

Search

Navigation