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Reaction of 1H-pyrrole-2,3-diones with malononitrile and aminocyclohexenones: synthesis of spiro[pyrrole-3,4′-quinolines]

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Abstract

New polyhydroquinolines spiroannulated with the pyrrol-2-one moiety were synthesized by the 4-dimethylaminopyridine-catalyzed three-component reaction of 1H-pyrrole-2,3-diones with malononitrile and aminocyclohexenones. The synthesized polyhydroquinolines exhibit antioxidant activity.

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References

  1. U. Rose, Arch. Pharm. (Weinheim, Ger.), 1990, 323, 281; DOI: https://doi.org/10.1002/ardp.19903230506.

    Article  CAS  Google Scholar 

  2. W. J. Elliott, C. V. Ram, J. Clin. Hypertens. (Greenwich, CT, U. S.), 2011, 13, 687; DOI: https://doi.org/10.1111/j.1751-7176.2011.00513.x.

    Article  CAS  Google Scholar 

  3. D. Takahashi, L. Oyunzul, S. Onoue, Y. Ito, S. Uchida, R. Simsek, M. G. Gunduz, C. Safak, S. Yamada, Biol. Pharm. Bull., 2008, 31, 473; DOI: https://doi.org/10.1248/bpb.31.473.

    Article  CAS  Google Scholar 

  4. K. Wellington, L. J. Scott, Drugs, 2003, 63, 2613; DOI: https://doi.org/10.2165/00003495-200363230-00004.

    Article  CAS  Google Scholar 

  5. S. A Khedkar, P. B. Auti, Mini-Rev. Med. Chem., 2014, 14, 282; DOI: https://doi.org/10.2174/138955706777698606.

    Article  CAS  Google Scholar 

  6. N. Edraki, A. R. Mehdipour, M. Khoshneviszadeh, R. Miri, Drug Discovery Today, 2009, 14, 1058; DOI: https://doi.org/10.1016/j.drudis.2009.08.004.

    Article  CAS  Google Scholar 

  7. D. Schade, M. Lanier, E. Willems, K. Okolotowicz, P. Bushway, C. Wahlquist, J. R. Cashman, J. Med. Chem., 2012, 55, 9946; DOI: https://doi.org/10.1021/jm301144g.

    Article  CAS  Google Scholar 

  8. I. Jacquemond-Collet, F. Benoit-Vical, M. Valentin, A. Stanislas, E. Mallié, M. Fourasté, Planta Med., 2002, 68, 68; DOI: https://doi.org/10.1055/s-2002-19869.

    Article  CAS  Google Scholar 

  9. P. J. Houghton, Y. Watabe, T. Z. Woldemariam, M. Yates, J. Pharm. Pharmacol., 1998, 50, 230; DOI: https://doi.org/10.1111/j.2042-7158.1998.tb02430.x.

    Article  CAS  Google Scholar 

  10. M. Mokhtar, K. S. Alghamdi, N. S. Ahmed, D. Bakhotmah, T. S. Saleh, J. Enzyme Inhib. Med. Chem., 2021, 36, 1454; DOI: https://doi.org/10.1080/14756366.2021.1944126.

    Article  Google Scholar 

  11. N. H. Sapariya, B. K. Vaghasiya, R. P. Thummar, R. D. Kamani, K. H. Patel, P. Thakor, S. S. Thakkar, A. Ray, D. K. Raval, New J. Chem., 2017, 41, 10686; DOI: https://doi.org/10.1039/C7NJ01962A.

    Article  CAS  Google Scholar 

  12. V. K. Sharma, S. K. Singh, RSC Adv., 2017, 7, 2682; DOI: https://doi.org/10.1039/C6RA24823C.

    Article  CAS  Google Scholar 

  13. J. P. Wan, Y. Liu, RSC Adv., 2012, 2, 9763; DOI: https://doi.org/10.1039/C2RA21406G.

    Article  CAS  Google Scholar 

  14. V. A. Mamedov, L. V. Mustakimova, O. A. Gerasimov, A. T. Gubaidullin, Russ. Chem. Bull., 2020, 69, 517; DOI: https://doi.org/10.1007/s11172-020-2792-9.

    Article  CAS  Google Scholar 

  15. S. S. Shatokhin, V. A. Tuskaev, S. Ch. Gagieva, É. T. Oganesyan, Russ. Chem. Bull., 2021, 70, 1011; DOI: https://doi.org/10.1007/s11172-021-3183-6.

    Article  CAS  Google Scholar 

  16. S. R. Kang, Y. R. Lee, Synthesis, 2013, 45, 2593; DOI: https://doi.org/10.1055/s-0033-1338506.

    Article  CAS  Google Scholar 

  17. Z. Elyasi, J. S. Ghomi, G. R. Najafi, Ultrason. Sonochem., 2021, 75, 105614; DOI: https://doi.org/10.1016/j.ultsonch.2021.105614.

    Article  CAS  Google Scholar 

  18. Q. N. Zhu, Y. C. Zhang, M. M. Xu, X. X. Sun, X. Yang, F. Shi, J. Org. Chem., 2016, 81, 7898. DOI: https://doi.org/10.1021/acs.joc.6b01598.

    Article  CAS  Google Scholar 

  19. T. Liu, Y. H. Lai, Y. Q. Yu, D. Z. Xu, New J. Chem., 2018, 42, 1046; DOI: https://doi.org/10.1039/c7nj03967k.

    Article  CAS  Google Scholar 

  20. M. V. Dmitriev, P. S. Silaichev, A. N. Maslivets, Russ. J. Org. Chem., 2015, 51, 74; DOI: https://doi.org/10.1134/S1070428015010121.

    Article  CAS  Google Scholar 

  21. M. V. Dmitriev, P. S. Silaichev, T. V. Sal’nikova, P. V. Melyukhin, A. N. Maslivets, Russ. J. Org. Chem., 2015, 51, 884; DOI: https://doi.org/10.1134/S1070428015060111.

    Article  CAS  Google Scholar 

  22. A. A. Sabitov, M. V. Dmitriev, A. I. Belozerova, T. V. Sal’nikova, A. N. Maslivets, Russ. J. Org. Chem., 2020, 56, 1217; DOI: https://doi.org/10.1134/S1070428020070155.

    Article  CAS  Google Scholar 

  23. T. V. Salnikova, A. A. Sabitov, M. V. Dmitriev, A. N. Maslivets, M. Rubin, Tetrahedron, 2021, 88, 132129; DOI: https://doi.org/10.1016/j.tet.2021.132129.

    Article  CAS  Google Scholar 

  24. F. P. Byrne, S. Jin, G. Paggiola, T. H. M. Petchey, J. H. Clark, T. J. Farmer, A. J. Hunt, C. R. McElroy, J. Sherwood, Sustainable Chem. Processes, 2016, 4, 7; DOI: https://doi.org/10.1186/s40508-016-0051-z.

    Article  Google Scholar 

  25. F. Shi, C. Li, M. Xia, K. Miao, Y. Zhao, S. Tu, W. Zheng, G. Zhang, N. Ma, Bioorg. Med. Chem. Lett., 2009, 19, 5565; DOI: https://doi.org/10.1016/j.bmcl.2009.08.046.

    Article  CAS  Google Scholar 

  26. H. G. Kathrotiya, M. P. Patel, Eur. J. Med. Chem., 2013, 63, 675; DOI: https://doi.org/10.1016/j.ejmech.2013.03.017.

    Article  CAS  Google Scholar 

  27. Wheat Antioxidants, Ed. Yu Liangli, John Wiley & Sons, Inc. Hoboken, NY, 2008, 276 pp.; DOI: https://doi.org/10.1002/9780470228333.

    Google Scholar 

  28. A. N. Maslivets, M. V. Dmitriev, S. Y. Balandina, A. A. Sabitov, T. V. Salnikova, Pat. RU 2743922, 2021.

  29. T. Sano, Y. Horiguchi, J. U. N. Toda, K. Imafuku, Y. Tsuda, Chem. Pharm. Bull., 1984, 32, 497; DOI: https://doi.org/10.1248/cpb.32.497.

    Article  CAS  Google Scholar 

  30. K. R. Scott, I. O. Edafiogho, E. L. Richardson, V. A. Farrar, J. A. Moore, E. I. Tietz, C. N. Hinko, H. Chang, A. El-Assadi, J. M. Nicholson, J. Med. Chem., 1993, 36, 1947; DOI: https://doi.org/10.1021/jm00066a003.

    Article  CAS  Google Scholar 

  31. CrysAlisPro, Version 1.171.37.33 (release 27-03-2014); Agilent Technologies.

  32. G. M. Sheldrick, Acta Crystallogr., Sect. A, 2008, 64, 112; DOI: https://doi.org/10.1107/S0108767307043930.

    Article  CAS  Google Scholar 

  33. L. Palatinus, G. Chapuis, J. Appl. Crystallogr., 2007, 40, 786; DOI: https://doi.org/10.1107/S0021889807029238.

    Article  CAS  Google Scholar 

  34. G. M. Sheldrick, Acta Crystallogr., Sect. C, 2015, 71, 3; DOI: https://doi.org/10.1107/S2053229614024218.

    Article  Google Scholar 

  35. O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard, H. Puschmann, J. Appl. Crystallogr., 2009, 42, 339; DOI: https://doi.org/10.1107/S0021889808042726.

    Article  CAS  Google Scholar 

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Correspondence to M. V. Dmitriev or A. N. Maslivets.

Additional information

This work was financially supported by the Perm World-Class Scientific and Educational Center “Rational Subsurface Use,” 2022.

No human or animal subjects were used in this research.

The authors declare no competing interests.

Based on the materials of the VI North Caucasus Organic Chemistry Symposium NCOCS-2022 (April 18–22, 2022, Stavropol).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2441–2450, November, 2022.

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Dmitriev, M.V., Moroz, A.A., Sabitov, A.A. et al. Reaction of 1H-pyrrole-2,3-diones with malononitrile and aminocyclohexenones: synthesis of spiro[pyrrole-3,4′-quinolines]. Russ Chem Bull 71, 2441–2450 (2022). https://doi.org/10.1007/s11172-022-3672-2

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  • DOI: https://doi.org/10.1007/s11172-022-3672-2

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