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Synthesis of 1-aryl-4,5-diphenyl-1H-imidazol-2(3H)-ones

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Abstract

The condensations of anilines (p-toluidine, 2-nitro-, 3-nitro-, and 4-nitroanilines), formaldehyde, and benzil monooxime were studied for the first time. 1-Aryl-4,5-diphenyl-1H-imidazol-2(3H)-ones (imidazolones) with 1-(3-nitro- and 4-nitro)phenyl substituents were prepared. 1-(p-Tolyl)imidazolone was synthesized by rearrangement of 3-hydroxy-4,5-diphenyl-1-(p-tolyl)-1H-imidazol-3-ium acetate under the action of Ac2O. The thermally induced rearrangement of 1-(3-nitrophenyl)-4,5-diphenyl-1H-imidazole 3-oxide to 1-(3-nitrophenyl)imidazolon was confirmed and the reaction mechanism was proposed.

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References

  1. M. M. Antonova, V. V. Baranov, A. N. Kravchenko, Chem. Heterocycl. Compd. (Engl. Transl.), 2015, 51, 395; DOI: https://doi.org/10.1007/s10593-015-1716-3.

    Article  CAS  Google Scholar 

  2. A. V. Finko, A. I. Sokolov, L. A. Vasilyeva, D. A. Skvortsov, A. S. H. Al-Khazraji, E. N. Ofitserov, N. V. Zyk, A. G. Majouga, E. K. Beloglazkina, Russ. Chem. Bull., 2021, 70, 457; DOI: https://doi.org/10.1007/s11172-021-3108-4.

    Article  CAS  Google Scholar 

  3. N. N. Makhova, L. I. Belen’kii, G. A. Gazieva, I. L. Dalinger, L. S. Konstantinova, V. V. Kuznetsov, A. N. Kravchenko, M. M. Krayushkin, O. A. Rakitin, A. M. Starosotnikov, L. L. Fershtat, S. A. Shevelev, V. Z. Shirinian, V N. Yarovenko, Russ. Chem. Rev. (Engl. Transl.), 2020, 89, 55; DOI: https://doi.org/10.1070/RCR4914.

    Article  CAS  Google Scholar 

  4. V. V. Baranov, M. M. Antonova, Yu. V. Nelyubina, I. E. Zanin, A. N. Kravchenko, N. N. Makhova, Mendeleev Commun., 2014, 3, 173; DOI: https://doi.org/10.1016/j.mencom.2014.04.017.

    Article  Google Scholar 

  5. M. M. Antonova, V. V. Baranov, Yu. V. Nelyubina, A. N. Kravchenko, Chem. Heterocycl. Compd. (Engl. Transl.), 2014, 50, 503; DOI: https://doi.org/10.1007/s10593-014-1501-8.

    Article  CAS  Google Scholar 

  6. 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 

  7. V. V. Baranov, M. M. Antonova, V. A. Karnoukhova, A. N. Kravchenko, Tetrahedron Lett., 2017, 58, 2203; DOI: https://doi.org/10.1016/j.tetlet.2017.04.061.

    Article  CAS  Google Scholar 

  8. G. Schwenker, H. Guo, S. Bernhart, Arch. Pharm. (Weiheim, Ger.), 1992, 325, 779; DOI: https://doi.org/10.1002/ardp.19923251207.

    Article  CAS  Google Scholar 

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

  10. V. V. Baranov, M. M. Antonova, Yu. V. Nelyubina, N. G. Kolotyrkina, A. N. Kravchenko, Synlett, 2017, 28, 669; DOI: https://doi.org/10.1055/s-0036-1588932.

    Article  CAS  Google Scholar 

  11. H. M. Chawla, M. Pathak, Tetrahedron, 1990, 46, 1331; DOI: https://doi.org/10.1016/S0040-4020(01)86697-7.

    Article  CAS  Google Scholar 

  12. C. W. Plummer, P. E. Finke, S. G. Mills, J. Wang, X. Tong, G. A. Doss, T. M. Fong, J. Z. Lao, M.-T. Schaeffer, J. Chen, C.-P. Shen, D. S. Stribling, L. P. Shearman, A. M. Strack, L. H. T. Van der Ploeg, Bioorg. Med. Chem. Lett., 2015, 15, 1441; DOI: https://doi.org/10.1016/j.bmcl.2004.12.078.

    Article  Google Scholar 

  13. C. P. Whittle, Aust. J. Chem., 1980, 33, 1545; DOI: https://doi.org/10.1071/CH9801545.

    Article  CAS  Google Scholar 

  14. US Pat. 5179117, Chem. Abstrs., 1993, 118, 254933.

  15. H. G. Aurich, Justus Liebigs Ann. Chem., 1970, 732, 195; DOI: https://doi.org/10.1002/jlac.19707320117.

    Article  Google Scholar 

  16. Y. B. Kim, C. S. Kim, C. K. Lee, J. Heterocycl. Chem., 1994, 31, 1653; DOI: https://doi.org/10.1002/jhet.5570310663.

    Article  CAS  Google Scholar 

  17. B. Krieg, H. Lautenschlaeger, Justus Liebigs Ann. Chem., 1976, 1976, 208; DOI: https://doi.org/10.1002/jlac.197619760203.

    Article  Google Scholar 

  18. H. Ahlbrecht, H. Hanisch, Synthesis, 1973, 1973, 109; DOI: https://doi.org/10.1055/s-1973-22142.

    Article  Google Scholar 

  19. M. M. Antonova, V. V. Baranov, Yu. V. Nelyubina, A. N. Kravchenko, Chem. Heterocycl. Compd. (Engl. Transl.), 2014, 50, 1203; DOI: https://doi.org/10.1007/s10593-014-1583-3.

    Article  CAS  Google Scholar 

  20. G. G. Kleinspehn, J. A. Jung, S. A. Studniarz, J. Org. Chem., 1967, 32, 460; DOI: https://doi.org/10.1021/jo01288a045.

    Article  CAS  Google Scholar 

  21. D. Armesto, W. M. Horspool, M. Apoita, M. G. Gallego, A. Ramos, Synthesis, 1989, 21, 448; DOI: https://doi.org/10.1055/s-1989-27283.

    Article  Google Scholar 

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    V. V. Baranov, V. V. Rusak & A. N. Kravchenko

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  1. V. V. Baranov
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  2. V. V. Rusak
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  3. A. N. Kravchenko
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Correspondence to V. V. Baranov.

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Devoted to Academician of the Russian Academy of Science V. A. Tartakovsky on the occasion of his 90th birthday.

No human or animal subjects were used in this research.

The authors declare no competing interests.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 2016–2020, September, 2022.

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Baranov, V.V., Rusak, V.V. & Kravchenko, A.N. Synthesis of 1-aryl-4,5-diphenyl-1H-imidazol-2(3H)-ones. Russ Chem Bull 71, 2016–2020 (2022). https://doi.org/10.1007/s11172-022-3623-y

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  • DOI: https://doi.org/10.1007/s11172-022-3623-y

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