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.
Similar content being viewed by others
References
Kaes, C.; Katz, A.; Hosseini, M. W. Chem. Rev. 2000, 100, 3553.
Zhang, H.; Toy, P. H. Adv. Synth. Catal. 2021, 363, 215.
Bazzini, C.; Giarrusso, A.; Porri, L. Macromol. Rapid Commun. 2002, 23, 922.
Zhang, J. F.; Bhuniya, S.; Lee, Y. H.; Bae, C.; Lee, J. H.; Kim, J. S. Tetrahedron Lett. 2010, 51, 3719.
Hagimori, M.; Uto, T.; Mizuyama, N.; Temma, T.; Yamaguchi, Y.; Tominaga, Y.; Saji, H. Sens. Actuators, B 2013, 181, 823.
Bagheri, M.; Tabatabae Far, M. A.; Mirzaei, H.; Ghasemi, F. Fundam. Clin. Pharmacol. 2019, 34, 51.
Jang, J.; Song, J.; Lee, H.; Sim, I.; Kwon, Y. V.; Jho, E.-h.; Yoon, Y. Exp. Mol. Med. 2021, 53, 407.
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.
Duric, S.; Tzschucke, C. C. Org. Lett. 2011, 13, 2310.
Jing, L.; Tang, Y.; Xiao, Z. Bioorg. Med. Chem. Lett. 2018, 28, 1386.
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.
Downs, R. P.; Chin, A. L.; Dean, K. M.; Carrick, J. D. J. Heterocycl. Chem. 2017, 54, 3008.
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.
Hapke, M.; Brandt, L.; Lützen, A. Chem. Soc. Rev. 2008, 37, 2782.
Samann, C.; Schade, M. A.; Yamada, S.; Knochel, P. Angew. Chem., Int. Ed. 2013, 52, 9495.
Markovic, T.; Murray, P. R. D.; Rocke, B. N.; Shavnya, A.; Blakemore, D. C.; Willis, M. C. J. Am. Chem. Soc. 2018, 140, 15916.
Campeau, L.-C.; Fagnou, K. Chem. Soc. Rev. 2007, 36, 1058.
Zhou, M.; Tsien, J.; Qin, T. Synlett, 2020, 31, 1962.
Han, Z.; Lv, J.; Zhang, J. Tetrahedron 2019, 75, 2162.
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.
Ievlev, M. Yu.; Mayorov, N. S.; Shishlikova, M. A.; Belikov, M. Yu.; Bardasov, I. N.; Ershov, O. V. Chem. Heterocycl. Compd. 2021, 57, 1051.
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.
Arafa, W. A. A.; Hussein, M. F. Chin. J. Chem. 2020, 38, 501.
Kurt, Z. B. Mol. Diversity 2019, 23, 625.
Jorns, M. S.; Jackson, M. R.; Cox, K. D.; Lam, P. Y. S.; Baugh, S. D. P. WO Patent 2020146636A1, 2020.
Karimi, F.; Yarie, M.; Zolfigol, M. A. Mol. Catal. 2020, 497, 111201.
Rubtsov, A. E.; Malkov, A. V. Synthesis 2021, 53, 2559.
Hagui, W.; Periasamy, K.; Soulé, J.-F. Eur. J. Org. Chem. 2021, 5388.
Gouda, M. A.; Berghot, M. A.; Abd El Ghani, G. E.; Khalil, A. E.-G. M. Synth. Commun. 2013, 44, 297.
Litvinov, V. P. Russ. Chem. Rev. 2006, 75, 577.
Author information
Authors and Affiliations
Corresponding author
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2022, 58(6/7), 301–303
Rights and permissions
Springer Nature or its licensor holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.
About this article
Cite this article
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
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10593-022-03086-7