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Regioselective synthesis of 2-aryl-5-(polyfluoroalkyl)pyridazin-3-ones based on 2-arylhydrazinylidene 1,3-dicarbonyl compounds

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Abstract

Polyfluoroalkyl-containing 2-arylhydrazinylidene 1,3-dicarbonyl compounds cyclize with ethyl (triphenylphosphoranylidene)acetate chemo- and regioselectively at the polyfluoroacyl—hydrazone moiety to form 6-carbonyl-functionalized 2-aryl-5-(polyfluoroalkyl)-pyridazin-3-ones. The regioselectivity of cyclizations was studied by GC/MS.

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References

  1. R. Bansal, S. Thota, Med. Chem. Res., 2013, 22, 2539; DOI: https://doi.org/10.1007/s00044-012-0261-1.

    Article  CAS  Google Scholar 

  2. S. Dubey, P. A. Bhosle, Med. Chem. Res., 2015, 24, 3579; DOI: https://doi.org/10.1007/s00044-015-1398-5.

    Article  CAS  Google Scholar 

  3. W. Akhtar, M. Shaquiquzzaman, M. Akhter, G. Verma, M. F. Khan, M. M. Alam, Eur. J. Med. Chem., 2016, 123, 256; DOI: https://doi.org/10.1016/j.ejmech.2016.07.061.

    Article  CAS  PubMed  Google Scholar 

  4. J. Singh, D. Sharma, R. Bansal, Future Med. Chem., 2017, 9, 95; DOI: https://doi.org/10.4155/fmc-2016-0194.

    Article  CAS  PubMed  Google Scholar 

  5. Z.-X. He, Y.-P. Gong, X. Zhang, L.-Y. Ma, W. Zhao, Eur. J. Med. Chem., 2021, 209, 112946; DOI: https://doi.org/10.1016/j.ejmech.2020.112946.

    Article  CAS  PubMed  Google Scholar 

  6. J. Singh, V. Kumar, P. Silakari, S. Kumar, J. Heterocycl. Chem., 2022; DOI: https://doi.org/10.1002/jhet.4589.

  7. N. Haider, W. Holzer, Product Class 8: Pyridazines in Science of Synthesis (vol. 16), Eds Y. Yamamoto, I. Shinkai, Georg Thieme Verlag, Stuttgart, 2004, pp. 125–250; DOI: https://doi.org/10.1055/sos-SD-016-00192.

    Google Scholar 

  8. H. J. Bestmann, G. Schmid, D. Sandmeier, Tetrahedron Lett., 1980, 21, 2939; DOI: https://doi.org/10.1016/0040-4039(80)88002-6.

    Article  CAS  Google Scholar 

  9. N. R. Mohamed, M. M. T. El-Saidi, Y. M. Ali, M. H. Elnagdi, J. Heterocycl. Chem., 2007, 44, 1333; DOI: https://doi.org/10.1002/jhet.5570440615.

    Article  CAS  Google Scholar 

  10. H. V. Patel, K. A. Vyas, S. P. Pandey, F. Tavares, P. S. Fernandes, Synth. Commun., 1991, 21, 1021; DOI: https://doi.org/10.1080/00397919108019791.

    Article  CAS  Google Scholar 

  11. H. V. Patel, K. A. Vyas, S. P. Pandey, F. Tavares, P. S. Fernandes, Synth. Commun., 1991, 21, 1935; DOI: https://doi.org/10.1080/00397919108021785.

    Article  CAS  Google Scholar 

  12. S. Zhou, H. Liao, C. He, Y. Dou, M. Jiang, L. Ren, Y. Zhao, P. Gong, Eur. J. Med. Chem., 2014, 83, 581; DOI: https://doi.org/10.1016/j.ejmech.2014.06.068.

    Article  CAS  PubMed  Google Scholar 

  13. L. Wang, S. Xu, X. Chen, X. Liu, Y. Duan, D. Kong, D. Zhao, P. Zheng, Q. Tang, W. Zhu, Bioorg. Med. Chem., 2018, 26, 245; DOI: https://doi.org/10.1016/j.bmc.2017.11.039.

    Article  CAS  PubMed  Google Scholar 

  14. L. X. Wang, X. Liu, S. Xu, Q. Tang, Y. Duan, Z. Xiao, J. Zhi, L. Jiang, P. Zheng, W. Zhu, Eur. J. Med. Chem., 2017, 141, 538; DOI: https://doi.org/10.1016/j.ejmech.2017.10.027.

    Article  CAS  PubMed  Google Scholar 

  15. Q. Tang, L. Wang, Y. Duan, W. Wang, S. Huang, J. Zhi, S. Jia, W. Zhu, P. Wang, R. Luo, P. Zheng, Eur. J. Med. Chem., 2017, 133, 97; DOI: https://doi.org/10.1016/j.ejmech.2017.03.045.

    Article  CAS  PubMed  Google Scholar 

  16. D. O’Hagan, J. Fluorine Chem., 2010, 131, 1071; DOI: https://doi.org/10.1016/j.jfluchem.2010.03.003.

    Article  Google Scholar 

  17. W. K. Hagmann, J. Med. Chem., 2008, 51, 4359; DOI: https://doi.org/10.1021/jm800219f.

    Article  CAS  PubMed  Google Scholar 

  18. M. Inoue, Y. Sumii, N. Shibata, ACS Omega, 2020, 5, 10633; DOI: https://doi.org/10.1021/acsomega.0c00830.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  19. O. Kamble, R. Dandela, S. Shinde, Curr. Org. Chem., 2021, 25, 2650; DOI: https://doi.org/10.2174/1385272825666210531111123.

    Article  CAS  Google Scholar 

  20. L. V. Politanskaya, G. A. Selivanova, E. V. Panteleeva, E. V. Tretyakov, V. E. Platonov, P. V. Nikul’shin, A. S. Vinogradov, Y. V. Zonov, V. M. Karpov, T. V. Mezhenkova, A. V. Vasilyev, A. B. Koldobskii, O. S. Shilova, S. M. Morozova, Y. V. Burgart, E. V. Shchegolkov, V. I. Saloutin, V. B. Sokolov, A. Y. Aksinenko, V. G. Nenajdenko, M. Y. Moskalik, V. V. Astakhova, B. A. Shainyan, A. A. Tabolin, S. L. Ioffe, V. M. Muzalevskiy, E. S. Balenkova, A. V. Shastin, A. A. Tyutyunov, V. E. Boiko, S. M. Igumnov, A. D. Dilman, N. Y. Adonin, V. V. Bardin, S. M. Masoud, D. V. Vorobyeva, S. N. Osipov, E. V. Nosova, G. N. Lipunova, V. N. Charushin, D. O. Prima, A. G. Makarov, A. V. Zibarev, B. A. Trofimov, L. N. Sobenina, K. V. Belyaeva, V. Y. Sosnovskikh, D. L. Obydennov, S. A. Usachev, Russ. Chem. Rev., 2019, 88, 425; DOI: https://doi.org/10.1070/RCR4871.

    Article  CAS  Google Scholar 

  21. D. N. Bazhin, Yu. S. Kudyakova, Yu. O. Edilova, Ya. V. Burgart, V. I. Saloutin, Russ. Chem. Bull., 2022, 71, 1321; DOI: https://doi.org/10.1007/s11172-022-3539-6.

    Article  CAS  Google Scholar 

  22. J. Han, L. Kiss, H. Mei, A. M. Remete, M. Ponikvar-Svet, D. M. Sedgwick, R. Roman, S. Fustero, H. Moriwaki, V. A. Soloshonok, Chem. Rev., 2021, 121, 4678; DOI: https://doi.org/10.1021/acs.chemrev.0c01263.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  23. N. A. Elkina, E. V. Shchegolkov, Y. V. Burgart, N. A. Agafonova, A. N. Perminova, N. A. Gerasimova, G. F. Makhaeva, E. V. Rudakova, N. V. Kovaleva, N. P. Boltneva, O. G. Serebryakova, S. S. Borisevich, N. P. Evstigneeva, N. V. Zilberberg, N. V. Kungurov, V. I. Saloutin, J. Fluorine Chem., 2022, 254, 109935; DOI: https://doi.org/10.1016/j.jfluchem.2021.109935.

    Article  CAS  Google Scholar 

  24. Y. V. Burgart, N. A. Elkina, E. V. Shchegolkov, O. P. Krasnykh, G. F. Makhaeva, G. A. Triandafilova, S. Y. Solodnikov, N. P. Boltneva, E. V. Rudakova, N. V. Kovaleva, O. G. Serebryakova, M. V. Ulitko, S. S. Borisevich, N. A. Gerasimova, N. P. Evstigneeva, S. A. Kozlov, Y. V. Korolkova, A. S. Minin, A. V. Belousova, E. S. Mozhaitsev, A. M. Klabukov, V. I. Saloutin, Molecules, 2022, 28, 59; DOI: https://doi.org/10.3390/molecules28010059.

    Article  PubMed  PubMed Central  Google Scholar 

  25. O. G. Khudina, N. A. Elkina, Ya. V. Burgart, M. A. Ezhikova, M. I. Kodess, Ya. L. Esaulkova, V. V. Zarubaev, A. A. Shtro, G. A. Triandafi lova, O. P. Krasnykh, K. O. Malysheva, N. A. Gerasimova, N. P. Evstigneeva, V. I. Saloutin, Russ. Chem. Bull., 2022, 71, 2670.

    Article  CAS  Google Scholar 

  26. N. A. Elkina, A. N. Perminova, N. A. Agafonova, E. V. Shchegolkov, Y. V. Burgart, M. G. Pervova, M. A. Samorukova, V. I. Saloutin, Russ. J. Gen. Chem., 2022, 92, 1591; DOI: https://doi.org/10.1134/S107036322209002X.

    Article  CAS  Google Scholar 

  27. O. G. Khudina, E. V. Shdiegol’kov, Y. V. Burgart, M. I. Kodess, V. I. Saloutin, O. N. Kazheva, G. V. Shilov, O. A. D’yachenko, M. A. Grishina, V. A. Potemkin, O. N. Chupakhin, Russ. J. Org. Chem., 2007, 43, 380; DOI: https://doi.org/10.1134/S1070428007030086.

    Article  CAS  Google Scholar 

  28. O. G. Khudina, Y. V. Burgart, E. V. Shchegol’kov, V. I. Saloutin, O. N. Kazheva, A. N. Chekhlov, O. A. D’yachenko, Russ. J. Org. Chem., 2009, 45, 801; DOI: https://doi.org/10.1134/S1070428009060013.

    Article  CAS  Google Scholar 

  29. G. F. Makhaeva, S. V. Lushchekina, N. P. Boltneva, O. G. Serebryakova, N. V. Kovaleva, E. V. Rudakova, N. A. Elkina, E. V. Shchegolkov, Y. V. Burgart, T. S. Stupina, A. A. Terentiev, E. V. Radchenko, V. A. Palyulin, V. I. Saloutin, S. O. Bachurin, R. J. Richardson, Eur. J. Med. Chem., 2021, 218, 113385; DOI: https://doi.org/10.1016/j.ejmech.2021.113385.

    Article  CAS  PubMed  Google Scholar 

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Authors and Affiliations

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

    N. A. Elkina, E. V. Shchegolkov, Ya. V. Burgart, A. N. Perminova & V. I. Saloutin

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  1. N. A. Elkina
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  2. E. V. Shchegolkov
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  3. Ya. V. Burgart
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  4. A. N. Perminova
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  5. V. I. Saloutin
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Corresponding author

Correspondence to V. I. Saloutin.

Additional information

Dedicated to Academician of the Russian Academy of Sciences I. P. Beletskaya on the occasion of her anniversary.

The study was carried out using the equipment of the Center for Joint use “Spectroscopy and Analysis of Organic Compounds” (CJU SAOC). The work was financially supported by the Ministry of Science and Higher Education of the Russian Federation (Government contract No. AAAA-A19-119011790132-7).

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, Vol. 72, No. 4, pp. 972–978, April, 2023.

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Elkina, N.A., Shchegolkov, E.V., Burgart, Y.V. et al. Regioselective synthesis of 2-aryl-5-(polyfluoroalkyl)pyridazin-3-ones based on 2-arylhydrazinylidene 1,3-dicarbonyl compounds. Russ Chem Bull 72, 972–978 (2023). https://doi.org/10.1007/s11172-023-3862-8

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  • DOI: https://doi.org/10.1007/s11172-023-3862-8

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