Skip to main content
SpringerLink
Log in

Synthesis of 4,5-Dialkyl-2-perfluoroaryl-1H-imidazol-1-ols and 4,5-Dimethyl-2-perfluoroaryl-1H-imidazoles

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

Aliphatic α-hydroxyamino oximes reacted with perfluoroaromatic aldehydes to give α-perfluoroaryl nitrones which underwent cyclization in acetic acid with the formation of 4,5-dialkyl-2-perfluoroaryl-1H-imidazol-1-ols. The latter were also obtained directly from aliphatic α-hydroxyamino oximes and perfluoro­aromatic aldehydes in acetic acid without isolation of intermediate nitrones. The reaction of 4,5-dimethyl-2-perfluoroaryl-1H-imidazol-1-ols with chloroacetone afforded 4,5-dimethyl-2-perfluoroaryl-1H-imidazoles.

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

Scheme
Scheme

Similar content being viewed by others

REFERENCES

  1. Guo, X.-X., Gu, D.-W., Wu, Z., and Zhan, W., Chem. Rev., 2015, vol. 115, p. 1622. https://doi.org/10.1021/cr500410y

    Article  CAS  PubMed  Google Scholar 

  2. Pietrasiak, E. and Lee, E., Synlett, 2020, vol. 31, p. 1349. https://doi.org/10.1055/s-0040-1707106

    Article  CAS  Google Scholar 

  3. Baykov, S., Semenov, A., Tarasenko, M., and Boyar­skiy, V.P., Tetrahedron Lett., 2020, vol. 61, article ID 152403. https://doi.org/10.1016/j.tetlet.2020.152403

  4. Zhang, X., Ashraf, M.A., Liu, Z., and Zhang, D., Synth. Commun., 2020, vol. 50, p. 2705. https://doi.org/10.1080/00397911.2020.1785504

    Article  CAS  Google Scholar 

  5. Lyubchuk, T.V. and Hordiyenko, O.V., Chem. Hetero­cycl. Compd., 2020, vol. 56, p. 1. https://doi.org/10.1007/s10593-020-02616-5

    Article  CAS  Google Scholar 

  6. Moseev, T.D., Varaksin, M.V., Gorlov, D.A., Charu­shin, V.N., and Chupakhin, O.N., J. Org. Chem., 2020, vol. 85, p. 11124. https://doi.org/10.1021/acs.joc.0c01042

    Article  CAS  PubMed  Google Scholar 

  7. Fujii, S., Maki, Y., and Kimoto, H., J. Fluorine Chem., 1989, vol. 43, p. 131. https://doi.org/10.1016/S0022-1139(00)81642-5

    Article  CAS  Google Scholar 

  8. Delgado-Rebollo, M., Garsía-Morales, C., Maya, C., Prieto, A., Echavarren, A.M., and Pérez, P.J., J. Organo­met. Chem., 2019, vol. 898, article ID 120856. https://doi.org/10.1016/j.jorganchem.2019.07.007

  9. Zhou, Y., Wang, J., Gu, Z., Wang, S., Zhu, W., Aceña, J.L., Soloshonok, V.A., Izawa, K., and Liu, H., Chem. Rev., 2016, vol. 116, p. 422. https://doi.org/10.1021/acs.chemrev.5b00392

    Article  CAS  PubMed  Google Scholar 

  10. Ali, I., Lone, M.N., and Aboul-Enein, H.Y., Med. Chem. Commun., 2017, vol. 8, p. 1742. https://doi.org/10.1039/c7md00067g

    Article  CAS  Google Scholar 

  11. Cornec, A.-S., Monti, L., Kovalevich, J., Makani, V., James, M.J., Vijayendran, K.G., Oukoloff, K., Yao, Y., Lee, V.M.-Y., Trojanowski, J.Q., Smith, A.B. III, Brunden, K.R., and Ballatore, C., J. Med. Chem., 2017, vol. 60, p. 5120. https://doi.org/10.1021/acs.jmedchem.7b00475

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  12. Baldwin, J.J., Engelhardt, E.L., Hirschmann, R., Lun­dell, G.F., Ponticello, G.S., Ludden, C.T., Sweet, C.S., Scriabine, A., Share, N.N., and Hall, R., J. Med. Chem., 1979, vol. 22, p. 687. https://doi.org/10.1021/jm00192a015

    Article  CAS  PubMed  Google Scholar 

  13. Akagane, K., Allan, G.G., Chopra, C.S., Friberg, T., Mattila, T., Omuircheartaigh, S., and Thomson, J.B., Suom. Kemistil. B, 1972, vol. 45, p. 223; Chem. Abstr., 1972, vol. 77, no. 126496z.

    CAS  Google Scholar 

  14. FRG Patent no. DE2254474, 1973; Chem. Abstr., 1973, vol. 79, no. 42507.

  15. Os’kina, I.A. and Tikhonov, A.Ya., Russ. J. Org. Chem., 2017, vol. 53, p. 236. https://doi.org/10.1134/S1070428017020166

    Article  Google Scholar 

  16. Os’kina, I.A. and Tikhonov, A.Ya., Russ. J. Org. Chem., 2017, vol. 53, p. 1239. https://doi.org/10.1134/S1070428017080139

    Article  Google Scholar 

  17. Nikolaenkova, E.B., Tikhonov, A.Ya., Amitina, S.A., and Gatilov, Yu.V., Chem. Heterocycl. Compd., 2014, vol. 50, p. 699. https://doi.org/10.1007/s10593-014-1523-2

    Article  CAS  Google Scholar 

  18. Nikolaenkova, E.B., Tikhonov, A.Ya., and Grishchen­ko, S.Yu., Chem. Heterocycl. Compd., 2019, vol. 55, p. 142. https://doi.org/10.1007/s10593-019-02430-8

    Article  CAS  Google Scholar 

  19. Nikitina, P.A. and Perevalov, V.P., Chem. Heterocycl. Compd., 2017, vol. 53, p. 123. https://doi.org/10.1007/s10593-017-2030-z

    Article  CAS  Google Scholar 

  20. Selivanov, B.A. and Tikhonov, A.Ya., Russ. Chem. Bull., Int. Ed., 2013, vol. 62, p. 1232. https://doi.org/10.1007/s11172-013-0169-z

    Article  CAS  Google Scholar 

  21. Vinogradov, A.S. and Platonov, V.E., Russ. J. Gen. Chem., 2020, vol. 90, p. 2264. https://doi.org/10.1134/S1070363220120087

    Article  CAS  Google Scholar 

  22. Grigor’eva, L.N., Volodarskii, L.B., and Tikho­nov, A.Ya., Izv. Sib. Otd. Akad. Nauk SSSR, Ser. Khim. Nauk, 1989, no. 3, p. 125.

    Google Scholar 

Download references

ACKNOWLEDGMENTS

Analytical and spectral data were obtained at the joint chemical research center, Siberian Branch, Russian Academy of Sciences.

Funding

This study was performed in the framework of state assignment for the Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences.

Author information

Authors and Affiliations

  1. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, 630090, Novosibirsk, Russia

    I. A. Os’kina, A. S. Vinogradov, B. A. Selivanov, V. A. Savelyev, V. E. Platonov & A. Ya. Tikhonov

Authors
  1. I. A. Os’kina
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. S. Vinogradov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. B. A. Selivanov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. V. A. Savelyev
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. V. E. Platonov
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. A. Ya. Tikhonov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to A. Ya. Tikhonov.

Ethics declarations

The authors declare the absence of conflict of interest.

Additional information

Translated from Zhurnal Organicheskoi Khimii, 2021, Vol. 57, No. 12, pp. 1752–1758 https://doi.org/10.31857/S0514749221120107.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Os’kina, I.A., Vinogradov, A.S., Selivanov, B.A. et al. Synthesis of 4,5-Dialkyl-2-perfluoroaryl-1H-imidazol-1-ols and 4,5-Dimethyl-2-perfluoroaryl-1H-imidazoles. Russ J Org Chem 57, 1968–1973 (2021). https://doi.org/10.1134/S1070428021120101

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428021120101

Keywords:

Search

Navigation