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N-Arylation of 1,2,4- and 1,3,4-Oxadiazolones under Activated Aromatic Nucleophilic Substitution Conditions

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Abstract

The possibilities of N-arylation of 1,2,4-oxadiazol-5(4H)-ones and 1,3,4-oxadiazol-2(3H)-ones with various electron-deficient chloro- and fluorine-substituted nitroarenes under the conditions of the classical activated nucleophilic substitution reaction were studied. A significant difference was found in the reactivity of 1,2,4- and 1,3,4-oxadiazolones in the N-arylation reactions. Methods for the synthesis of N-nitroaryl derivatives of 1,2,4- and 1,3,4-oxadiazolones, providing the target products of sufficient purity in yields of about 65–96%, were developed.

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REFERENCES

  1. Moser, P.C., Bergis, O.E., Jegham, S., Lochead, A., Duconseille, E., Terranova, J.P., Caille, D., Berque-Bestel, I., Lezoualc, H.F., Fischmeister, R., Dumuis, A., Bockaert, J., George, P., Soubrié, P., and Scatton, B., J. Pharmacol. Exp. Ther., 2002, vol. 302, p. 731. https://doi.org/10.1124/jpet.102.034249

    Article  CAS  PubMed  Google Scholar 

  2. Shah, S.K., He, S., Guo, L., Truong, Q., Qi, H., Du, W., Lai, Z., Liu, J., Jian, T., Hong, Q., Dobbelaar, P., Ye, Z., Sherer, E., Feng, Z., Yu, Y., Wong, F., Samuel, K., Madiera, M., Karanam, B.V., Reddy, V.B., Mitelman, S., Tong, S.X., Chicchi, G.G., Tsao, K.L., Trusca, D., Feng, Y., Wu, M., Shao, Q., Trujillo, M.E., Eiermann, G.J., Li, C., Pachanski, M., Fernandez, G., Nelson, D., Bunting, P., Morissette, P., Volksdorf, S., Kerr, J., Zhang, B.B., Howard, A.D., Zhou, Y.P., Pasternak, A., Nargund, R.P., and Hagmann, W.K., ACS Med. Chem. Lett., 2015, vol. 6, p. 513. https://doi.org/10.1021/ml500514w

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  3. Baker, W.L. and White, W.B., Ann. Pharmacother., 2011, vol. 45, p. 1506. https://doi.org/10.1345/aph.1Q468

    Article  CAS  PubMed  Google Scholar 

  4. Haffar, O., Dubrovsky, L., Lowe, R., Berro, R., Kashanchi, F., Godden, J., Vanpouille, C., Bajorath, J., and Bukrinsky, M., J. Virol., 2005, vol. 79, p. 13028. https://doi.org/10.1128/JVI.79.20.13028-13036.2005

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  5. Ohmoto, K., Okuma, M., Yamamoto, T., Kijima, H., Sekioka, T., Kitagawa, K., Yamamoto, S., Tanaka, K., Kawabata, K., Sakata, A., Imawaka, H., Nakai, H., and Toda, M., Bioorg. Med. Chem., 2001, vol. 9, p. 1307. https://doi.org/10.1016/s0968-0896(01)00007-4

    Article  CAS  PubMed  Google Scholar 

  6. Bi, F., Song, D., Qin, Y., Liu, X., Teng, Y., Zhang, N., Zhang, P., Zhang, N., and Ma, S., Bioorg. Med. Chem., 2019, vol. 27, p. 3179. https://doi.org/10.1016/j.bmc.2019.06.010

    Article  CAS  PubMed  Google Scholar 

  7. Marvadi, S.K., Krishna, V.S., Sinegubova, E.O., Volobueva, A.S., Esaulkova, Y.L., Muryleva, A.A., Tentler, D.G., Sriram, D., Zarubaev, V.V., and Kantevari, S., Bioorg. Med. Chem. Lett., 2019, vol. 29, p. 2664. https://doi.org/10.1016/j.bmcl.2019.07.040

    Article  CAS  PubMed  Google Scholar 

  8. Yue, E.W., Sparks, R., Polam, P., Modi, D., Douty, B., Wayland, B., Glass, B., Takvorian, A., Glenn, J., Zhu, W., Bower, M., Liu, X., Leffet, L., Wang, Q., Bowman, K.J., Hansbury, M.J., Wei, M., Li, Y., Wynn, R., Burn, T.C., Koblish, H.K., Fridman, J.S., Emm, T., Scherle, P.A., Metcalf, B., and Combs, A.P., ACS Med. Chem. Lett., 2017, vol. 8, p. 486. https://doi.org/10.1021/acsmedchemlett.6b00391

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  9. Phakhodee, W., Duangkamol, C., Wiriya, N., and Pattarawarapan, M., RSC Adv., 2018, vol. 8, p. 38281. https://doi.org/10.1039/C8RA08207C

    Article  CAS  PubMed  PubMed Central  ADS  Google Scholar 

  10. Zhou, L., Li, H., Zhang, W., and Wang, L., Chem. Commun., 2018, vol. 54, p. 4822. https://doi.org/10.1039/C8CC00124C

    Article  CAS  Google Scholar 

  11. Sauer, J. and Mayer, K.K., Tetrahedron Lett., 1968, vol. 9, p. 325. https://doi.org/10.1016/s0040-4039(01)98754-4

    Article  Google Scholar 

  12. Soldatova, N., Semenov, A., Geyl, K., Baykov, S., Shetnev, A., Konstantinova, A., Korsakov, M., Yusubov, M., and Postnikov, P., Adv. Synth. Catal., 2021, vol. 363, p. 1. https://doi.org/10.1002/adsc.202100426

    Article  CAS  Google Scholar 

  13. Baykov, S., Sharonova, T., Shetnev, A., Rozhkov, S., Kalinin, S., and Smirnov, A., Tetrahedron, 2017, vol. 73, p. 945. https://doi.org/10.1016/j.tet.2017.01.007

    Article  CAS  Google Scholar 

  14. Musser, J.H., Brown, R.E., Love, B., Bailey, K., Jones, H., Kahen, R., Huang, F., Khandwala, A., Leibowitz, M., Sonnino-Goldman, P., and Donigi-Ruzza, D., J. Med. Chem., 1984, vol. 27, p. 121. https://doi.org/10.1021/jm00368a004

    Article  CAS  PubMed  Google Scholar 

  15. Van der Linden, L., Vives-Adrian, L., Selisko, B., Ferrer-Orta, C., Liu, X., Lanke, K., Ulferts, R., De Palma, A.M., Tanchis, F., Goris, N., Lefebvre, D., De Clercq, K., Leyssen, P., Lacroix, C., Purstinger, G., Coutard, B., Canard, B., Boehr, D.D., Arnold, J.J., Cameron, C.E., Verdaguer, N., Neyts, J., and van Kuppeveld, F.J., PLoS Pathog., 2015, vol. 11, p. 1. https://doi.org/10.1371/journal.ppat.1004733

    Article  CAS  Google Scholar 

  16. Hughes, G. and Bryce, M.R., J. Mater. Chem., 2005, vol. 15, p. 94. https://doi.org/10.1039/B413249C

    Article  CAS  Google Scholar 

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Funding

The work was financially supported by the Russian Science Foundation (project no. 22-23-20158). The authors are grateful to the Center for Chemical Analysis and Materials Research and the Research Center for X-ray Diffraction Studies, Research Park, St. Petersburg State University, for mass spectrometric analysis.

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Authors and Affiliations

  1. Pharmaceutical Technology Transfer Center, Ushinskii Yaroslavl’ State Pedagogical University, 150000, Yaroslavl’, Russia

    A. S. Konstantinova & A. A. Shetnev

  2. Kosygin Russian State University (Technology. Design. Art), 119071, Moscow, Russia

    A. S. Konstantinova & M. K. Korsakov

  3. St. Petersburg Pasteur Institute, 197101, St. Petersburg, Russia

    A. S. Volobueva

Authors
  1. A. S. Konstantinova
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  2. A. A. Shetnev
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  3. A. S. Volobueva
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  4. M. K. Korsakov
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Corresponding authors

Correspondence to A. S. Konstantinova or A. A. Shetnev.

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Additional information

Translated from Zhurnal Organicheskoi Khimii, 2023, Vol. 59, No. 11, pp. 1435–1445 https://doi.org/10.31857/S0514749223110058.

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Konstantinova, A.S., Shetnev, A.A., Volobueva, A.S. et al. N-Arylation of 1,2,4- and 1,3,4-Oxadiazolones under Activated Aromatic Nucleophilic Substitution Conditions. Russ J Org Chem 59, 1874–1883 (2023). https://doi.org/10.1134/S1070428023110052

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