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Synthesis of polyfunctional trifluoromethylated pyridones fused with the strained carbocyclic cores

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Abstract

A two-step synthesis of trifluoromethylated pyridones fused with different strained carbocyclic cores was developed. Acylation of the starting cyclic amino enones with ethyl malonyl chloride gave the corresponding amido enones that underwent the intramolecular Knoevenagel condensation to afford the target fused pyridones.

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References

  1. S. Purser, P. R. Moore, S. Swallow, V. Gouverneur, Chem. Soc. Rev., 2008, 37, 320; DOI: https://doi.org/10.1039/b610213c.

    Article  CAS  PubMed  Google Scholar 

  2. J. Nie, H.-Ch. Guo, D. Cahard, J.-An Ma, Chem. Rev., 2011, 111, 455; DOI: https://doi.org/10.1021/cr100166a.

    Article  CAS  PubMed  Google Scholar 

  3. I. Katsuyama, J. Synth. Org. Chem., Jpn., 2009, 67, 992; DOI: https://doi.org/10.5059/yukigoseikyokaishi.67.992.

    Article  CAS  Google Scholar 

  4. G. G. Furin, Ftorsoderzhashchie geterocyclicheskie soedineniya [Fluorinated Heterocyclic Compounds], Nauka, Novosibirsk, 2001, 304 pp. (in Russian).

    Google Scholar 

  5. L. M. Yagupol’sky, Aromatisheskie i geterocyclicheskie soedineniya s ftorsoderzhashchimi zamestitelyami [Aromatic Heterocyclic Compounds bearing Fluorinated Substituents], Naukova Dumka, Kiïv, 1988, 275 pp. (in Russia).

    Google Scholar 

  6. V. Nenajdenko, Fluorine in Heterocyclic Chemistry, Springer, Cham—Heidelberg—New York—Dordrecht—London, 2014, Vol. 1, 681 pp.; Vol. 2, 760 pp.

    Book  Google Scholar 

  7. M. S. Wiehn, E. V. Vinogradova, A. Togni, J. Fluorine Chem., 2010, 131, 951; DOI: https://doi.org/10.1016/j.jfluchem.2010.06.020.

    Article  CAS  Google Scholar 

  8. A. Matsnew, Sh. Noritake, Y. Nomura, E. Tokunaga, Sh. Nakamura, N. Shibata, Angew. Chem., Int. Ed., 2010, 49, 572; DOI: https://doi.org/10.1002/anie.200905225.

    Article  Google Scholar 

  9. D. A. Nagib, D. W. C. MacMillan, Nature, 2011, 480, 224; DOI: https://doi.org/10.1038/nature10647.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  10. P.-Z. Zhang, Ch.-K. Li, G.-Yu Zhang, L. Zhang, Y.-J. Jiang, J.-P. Zou, Tetrahedron, 2016, 72, 3250; DOI: https://doi.org/10.1016/j.tet.2016.04.048.

    Article  CAS  Google Scholar 

  11. V. Krishnamurti, S. Munoz, X. Ispizua-Rodriguez, J. Vickerman, T. Mathew, G. K. Surya Prakash, Chem. Commun., 2018, 54, 10574; DOI: https://doi.org/10.1039/C8CC04907F.

    Article  CAS  Google Scholar 

  12. S. V. Druzhinin, E. S. Balenkova, V. G. Nenajdenko, Tetrahedron, 2007, 63, 7753; DOI: https://doi.org/10.1016/j.tet.2007.04.029.

    Article  CAS  Google Scholar 

  13. B. Jiang, J.-J. Dong, Y. Jin, X.-l. Du, M. Xu, Eur. J. Org. Chem., 2008, 2693; DOI: https://doi.org/10.1002/ejoc.200800121.

  14. B. Jiang, Yu-G. Si, J. Org. Chem., 2002, 67, 9449; DOI: https://doi.org/10.1021/jo0204606.

    Article  CAS  PubMed  Google Scholar 

  15. P. Czerwinski, M. Michalak, J. Org. Chem., 2017, 82, 7980; DOI: https://doi.org/10.1021/acs.joc.7b01235.

    Article  CAS  PubMed  Google Scholar 

  16. A. Yu. Mitrofanov, V. A. Bychkova, S. E. Nefedov, I. P. Beletskaya, J. Org. Chem., 2020, 85, 14507; DOI: https://doi.org/10.1021/acs.joc.0c00913.

    Article  CAS  PubMed  Google Scholar 

  17. E. Okada, T. Kinomura, Yu. Higashiyama, H. Takeuchi, M. Hojo, Heterocycles, 1997, 46, 129; DOI: https://doi.org/10.3987/COM-97-S45.

    Article  CAS  Google Scholar 

  18. O. A. Kuznetsova, V. I. Filyakov, K. I. Pashkevich, E. N. Ulomskii, P. V. Plehanov, G. L. Rusinov, M. I. Kodess, V. L. Rusinov, Russ. Chem. Bull., 2003, 52, 1190; DOI: https://doi.org/10.1023/A:1024777828344.

    Article  CAS  Google Scholar 

  19. C. Plaçais, M. Donnard, A. Panossian, J.-P. Vors, D. Bernier, S. Pazenok, F. Leroux, Org. Lett., 2021, 23, 4915; DOI: https://doi.org/10.1021/acs.orglett.1c01672.

    Article  PubMed  Google Scholar 

  20. V. I. Filyakova, N. S. Boltacheva, M. G. Pervovaa, V. N. Charushin, Mendeleev Commun., 2021, 31, 388; DOI: https://doi.org/10.1016/j.mencom.2021.05.035.

    Article  CAS  Google Scholar 

  21. P. A. Slepukhin, N. S. Boltacheva, M. G. Pervova, V. I. Filyakova, V. N. Charushin, Russ. Chem. Bull., 2022, 69, 2355; DOI: https://doi.org/10.1007/s11172-020-3030-1.

    Article  Google Scholar 

  22. [A. B. Koldobskii, N. P. Tsvetkov, P. V. Verteletskii, I. A. Godovikov, V. N. Kalinin, Russ. Chem. Bull., 2009, 58, 1431; DOI: https://doi.org/10.1007/s11172-009-0191-3.

    Article  CAS  Google Scholar 

  23. A. B. Koldobskii, N. P. Tsvetkov, E. V. Solodova, V. N. Kalinin, J. Fluorine Chem., 2010, 131, 714; DOI: https://doi.org/10.1016/j.jfluchem.2010.03.006.

    Article  CAS  Google Scholar 

  24. A. B. Koldobskii, N. P. Tsvetkov, E. V. Solodova, V. N. Kalinin, J. Fluorine Chem., 2010, 131, 852; DOI: https://doi.org/10.1016/j.jfluchem.2010.04.007.

    Article  CAS  Google Scholar 

  25. A. B. Koldobskii, O. S. Shilova, E. V. Solodova, P. V. Verteletskii, I. A. Godovikov, V. N. Kalinin, J. Fluorine Chem., 2018, 207, 7; DOI: https://doi.org/10.1016/j.jfluchem.2017.12.007.

    Article  CAS  Google Scholar 

  26. A. B. Koldobskii, E. V. Solodova, I. A. Godovikov, P. V. Verteletskii, V. N. Kalinin, J. Fluorine Chem., 2010, 131, 873; DOI: https://doi.org/10.1016/j.jfluchem.2010.05.015.

    Article  CAS  Google Scholar 

  27. Y. Zhang, A. Pike, Bioorg. Med. Chem. Lett., 2021, 38, 127849; DOI: https://doi.org/10.1016/j.bmcl.2021.127849.

    Article  CAS  PubMed  Google Scholar 

  28. R. Fiorafanti, J. Stari, C. Zwergel, S. Walente, A. Mai, Chem. Rec., 2018, 18, 1818; DOI: https://doi.org/10.1002/tcr.201800091.

    Article  Google Scholar 

  29. Si Wen, Y. Chen, Q. Tian, Y. Zhang, G. Cheng, J. Org. Chem., 2022, 87, 1124; DOI: https://doi.org/10.1021/acs.joc.1c02464.

    Article  CAS  PubMed  Google Scholar 

  30. J. W. Tilley, A. Sidduri, J. Lou, G. Kaplan, N. Tare, G. Cavallo, K. Frank, A. Pamidimukkala, D. S. Choi, L. Gerber, A. Railkar, L. Renzetti, Bioorg. Med. Chem. Lett., 2013, 23, 1036; DOI: https://doi.org/10.1016/j.bmcl.2012.12.019.

    Article  CAS  PubMed  Google Scholar 

  31. H.-P. Guan, C.-M. Hu, Synthesis, 1996, 11, 1363; DOI: https://doi.org/10.1055/s-1996-4393.

    Article  Google Scholar 

  32. W. Yan, R. Wang, T. Zhang, H. Deng, J. Chen, W. Wu, Zh. Weng, Org. Biomol. Chem., 2018, 16, 9440; DOI: https://doi.org/10.1039/C8OB02701C.

    Article  CAS  PubMed  Google Scholar 

  33. Organic Synthesis Based on Name Reactions and Unnamed Reactions, Eds A. Hassner, C. Stumer, Elsevier, Tokyo—Oxford—New York, 1994, Vol. 11, 453 pp.

    Google Scholar 

  34. L. Töke, Z. Hell, G. T. Szabó, G. Tóth, M. Bihari, A. Rockenbauer, Tetrahedron, 1993, 49, 5133; DOI: https://doi.org/10.1016/S0040-4020(01)81878-0.

    Article  Google Scholar 

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Funding

This work was financially supported by the Russian Science Foundation (Project No. 22-23-00887).

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Correspondence to A. B. Koldobskii.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 2224–2230, October, 2022.

No human or animal subjects were used in this research.

The authors declare no competing interests.

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Koldobskii, A.B., Shilova, O.S., Glazun, S.A. et al. Synthesis of polyfunctional trifluoromethylated pyridones fused with the strained carbocyclic cores. Russ Chem Bull 71, 2224–2230 (2022). https://doi.org/10.1007/s11172-022-3649-1

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  • DOI: https://doi.org/10.1007/s11172-022-3649-1

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