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Modern Methods for the Synthesis of Cyano-Substituted Bipyridine Derivatives (microreview)

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Chemistry of Heterocyclic Compounds Aims and scope

This microreview summarizes the most frequently employed methods for the synthesis of cyano-substituted bipyridine derivatives over the past 5 years. Most of the approaches to the preparation of such compounds described in the literature are based on cross-coupling reactions, heterocyclization of pyridine-containing substrates, and various multicomponent processes.

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References

  1. Kaes, C.; Katz, A.; Hosseini, M. W. Chem. Rev. 2000, 100, 3553.

    Article  CAS  Google Scholar 

  2. Zhang, H.; Toy, P. H. Adv. Synth. Catal. 2021, 363, 215.

    Article  CAS  Google Scholar 

  3. Bazzini, C.; Giarrusso, A.; Porri, L. Macromol. Rapid Commun. 2002, 23, 922.

    Article  CAS  Google Scholar 

  4. Zhang, J. F.; Bhuniya, S.; Lee, Y. H.; Bae, C.; Lee, J. H.; Kim, J. S. Tetrahedron Lett. 2010, 51, 3719.

    Article  CAS  Google Scholar 

  5. Hagimori, M.; Uto, T.; Mizuyama, N.; Temma, T.; Yamaguchi, Y.; Tominaga, Y.; Saji, H. Sens. Actuators, B 2013, 181, 823.

    Article  CAS  Google Scholar 

  6. Bagheri, M.; Tabatabae Far, M. A.; Mirzaei, H.; Ghasemi, F. Fundam. Clin. Pharmacol. 2019, 34, 51.

    Article  Google Scholar 

  7. Jang, J.; Song, J.; Lee, H.; Sim, I.; Kwon, Y. V.; Jho, E.-h.; Yoon, Y. Exp. Mol. Med. 2021, 53, 407.

  8. Gao, Y.; Horti, A. G.; Kuwabara, H.; Ravert, H. T.; Hilton, J.; Holt, D. P.; Kumar, A.; Alexander, M.; Endres, C. J.; Wong, D. F.; Dannals, R. F. J. Med. Chem. 2007, 50, 3814.

    Article  CAS  Google Scholar 

  9. Duric, S.; Tzschucke, C. C. Org. Lett. 2011, 13, 2310.

    Article  CAS  Google Scholar 

  10. Jing, L.; Tang, Y.; Xiao, Z. Bioorg. Med. Chem. Lett. 2018, 28, 1386.

    Article  CAS  Google Scholar 

  11. Nakamura, R. L.; Burlingame, M. A.; Yang, S.; Crosby, D. C.; Talbot, D. J.; Chui, K.; Frankel, A. D.; Renslo, A. R. Antimicrob. Agents Chemother. 2017, 61.

  12. Downs, R. P.; Chin, A. L.; Dean, K. M.; Carrick, J. D. J. Heterocycl. Chem. 2017, 54, 3008.

    Article  CAS  Google Scholar 

  13. Tahir, N.; Muniz-Miranda, F.; Everaert, J.; Tack, P.; Heugebaert, T.; Leus, K.; Vincze, L.; Stevens, C. V.; Van Speybroeck, V.; Van Der Voort, P. J. Catal. 2019, 371, 135.

    Article  CAS  Google Scholar 

  14. Hapke, M.; Brandt, L.; Lützen, A. Chem. Soc. Rev. 2008, 37, 2782.

    Article  CAS  Google Scholar 

  15. Samann, C.; Schade, M. A.; Yamada, S.; Knochel, P. Angew. Chem., Int. Ed. 2013, 52, 9495.

    Article  Google Scholar 

  16. Markovic, T.; Murray, P. R. D.; Rocke, B. N.; Shavnya, A.; Blakemore, D. C.; Willis, M. C. J. Am. Chem. Soc. 2018, 140, 15916.

    Article  CAS  Google Scholar 

  17. Campeau, L.-C.; Fagnou, K. Chem. Soc. Rev. 2007, 36, 1058.

    Article  CAS  Google Scholar 

  18. Zhou, M.; Tsien, J.; Qin, T. Synlett, 2020, 31, 1962.

    Google Scholar 

  19. Han, Z.; Lv, J.; Zhang, J. Tetrahedron 2019, 75, 2162.

    Article  CAS  Google Scholar 

  20. Krinochkin, A. P.; Reddy, G. M.; Kopchuk, D. S.; Slepukhin, P. A.; Shtaitz, Y. K.; Khalymbadzha, I. A.; Kovalev, I. S.; Kim, G. A.; Ganebnykh, I. N.; Zyryanov, G. V.; Chupakhin, O. N.; Charushin, V. N. Mendeleev Commun. 2021, 31, 542.

    Article  CAS  Google Scholar 

  21. Ievlev, M. Yu.; Mayorov, N. S.; Shishlikova, M. A.; Belikov, M. Yu.; Bardasov, I. N.; Ershov, O. V. Chem. Heterocycl. Compd. 2021, 57, 1051.

    Article  CAS  Google Scholar 

  22. Ievlev, M. Yu.; Mayorov, N. S.; Shishlikova, M. A.; Belikov, M. Yu.; Bardasov, I. N.; Ershov, O. V. Russ. J. Org. Chem. 2021, 57, 1961.

    Google Scholar 

  23. Arafa, W. A. A.; Hussein, M. F. Chin. J. Chem. 2020, 38, 501.

    Article  CAS  Google Scholar 

  24. Kurt, Z. B. Mol. Diversity 2019, 23, 625.

    Article  Google Scholar 

  25. Jorns, M. S.; Jackson, M. R.; Cox, K. D.; Lam, P. Y. S.; Baugh, S. D. P. WO Patent 2020146636A1, 2020.

  26. Karimi, F.; Yarie, M.; Zolfigol, M. A. Mol. Catal. 2020, 497, 111201.

    Article  CAS  Google Scholar 

  27. Rubtsov, A. E.; Malkov, A. V. Synthesis 2021, 53, 2559.

    Article  CAS  Google Scholar 

  28. Hagui, W.; Periasamy, K.; Soulé, J.-F. Eur. J. Org. Chem. 2021, 5388.

  29. Gouda, M. A.; Berghot, M. A.; Abd El Ghani, G. E.; Khalil, A. E.-G. M. Synth. Commun. 2013, 44, 297.

    Article  Google Scholar 

  30. Litvinov, V. P. Russ. Chem. Rev. 2006, 75, 577.

    Article  CAS  Google Scholar 

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Correspondence to Mikhail Yu. Ievlev.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2022, 58(6/7), 301–303

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Mayorov, N.S., Ievlev, M.Y. Modern Methods for the Synthesis of Cyano-Substituted Bipyridine Derivatives (microreview). Chem Heterocycl Comp 58, 301–303 (2022). https://doi.org/10.1007/s10593-022-03086-7

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  • DOI: https://doi.org/10.1007/s10593-022-03086-7

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