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The synthesis of ortho-stilbazoles (2-styrylpyridines) (microreview)

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Chemistry of Heterocyclic Compounds Aims and scope

This microreview compiles methods for the synthesis of ortho-stilbazoles (2-styrylpyridines) described in the literature in 2017–2022. Depending on the synthons from which the target structure is formed, four main synthetic approaches can be distinguished: coupling reactions, Wittig reactions, condensation reactions, and pyridine ring formation reactions.

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References

  1. (a) Semenov, A. V.; Balakireva, O. I.; Tarasova, I. V.; Semenova, E. V.; Zulfugarov, P. K. Med. Chem. Res. 2020, 29, 1590. (b) Semenov, A. V.; Balakireva, O. I.; Tarasova, I. V.; Burtasov, A. A.; Semenova, E. V.; Petrov, P. S.; Minaeva, O. V.; Pyataev, N. A. Med. Chem. Res. 2018, 27, 1298. (c) Pugachev, M. V.; Pavelyev, R. S.; Nguyen, T. N. T.; Gabbasova, R. R.; Bulatov, T. M.; Iksanova, A. G.; Aljondi, B.; Bondar, O. V.; Grishaev, D. Yu., Yamaleeva, Z. R.; Kataeva, O. N.; Nikishova, T. V.; Balakin, K. V.; Shtyrlin, Y. G. Bioorg. Med. Chem. 2021, 30, 115957. (d) Chen, G.; Shan, W.; Wu, Y.; Ren, L.; Dong, J.; Ji, Z. Chem. Pharm. Bull. 2005, 53, 1587. (e) Li, Y.-Q.; Li, Z.-L.; Zhao, W.-J.; Wen, R.-X.; Meng, Q.-W.; Zeng, Y. Eur. J. Med. Chem. 2006, 41, 1084. (f) Sun, W.; Fang, S.; Yan, H. Med. Chem. Commun. 2018, 9, 1054. (g) Hrast, M.; Frlan, R.; Knez, D.; Zdovc, I.; Barreteau, H.; Gobec, S. Bioorg. Med. Chem. Lett. 2021, 40, 127966.

  2. (a) Zhang, X.-D.; Zhao, Y.; Chen, K.; Jiang, Y.-F.; Sun, W.-Y. Chem.–Asian J. 2019, 14, 3620. (b) Guan, R.; Chen, H.; Cao, F.; Cao, D.; Deng, Y. Inorg. Chem. Commun. 2013, 38, 112. (c) Xie, P.; Guo F.; Zhang, D.; Zhang, L. Chin. J. Chem. 2011, 29, 1975. (d) Zho, H.; Sun, L.; Chen, W.; Tian, G.; Chen, Y.; Li, Y.; Su, J. Tetrahedron 2016, 72, 2300. (e) Gabr, M. T.; Pigge, F. C. Dalton Trans. 2016, 45, 14039. (f) Zhang, X.-D.; Hua, J.-A.; Guo, J.-H.; Zhao, Y.; Sun, W.-Y. J. Mater. Chem. C 2018, 6, 12623. (g) Wang, M.-Q.; Ren, G.-Y.; Zhao, S.; Lian, G.-C.; Chen, T.-T.; Ci, Y.; Li, H.-Y. Spectrochim. Acta A: Mol. Biomol. Spectrosc. 2018, 199, 441. (h) Senthil, K.; Kalainathan, S.; Kumar, A. R.; Aravindan, P. G. RSC Adv. 2014, 4, 56112.

  3. (a) Savanur, H. M.; Kalkhambkar, R. G.; Laali, K .K. Appl. Catal. A: Gen. 2017, 543, 150. (b) Clauss, R.; Baweja, S.; Gelman, D.; Hey-Hawkins, E. Dalton Trans. 2022, 51, 1344. (c) Tan, G.; Das, M.; Maisuls, I.; Strassert, C. A.; Glorius, F. Angew. Chem., Int. Ed. 2021, 60, 15650.

  4. (a) Tian, J.-J.; Yang, Z.-Y.; Liang, X.-S.; Liu, N.; Hu, C.-Y.; Tu, X.-S.; Li, X.; Wang, X.-C. Angew. Chem., Int. Ed. 2020, 59, 18452. (b) Li, Q.-Q.; Shah, Z.; Qu, J.-P.; Kang, Y.-B. J. Org. Chem. 2018, 83, 296. (c) Cao, C.; Zeng, Z.; Cao, C. J. Phys. Org. Chem. 2022, 35(4), e4319.

  5. (a) Nguyen, T. B.; Nguyen, T. M.; Retailleau, P. Chem.–Eur. J. 2020, 26, 4682. (b) Sharma, R.; Abdullaha, M.; Bharate, S. B. J. Org. Chem. 2017, 82, 9786.

  6. (a) Chen, C.-H.; Wu, Q.-Y.; Wei, C.; Liang, C.; Su, G.-F.; Mo, D.-L. Green Chem. 2018, 20, 2722. (b) Yamada, T.; Hashimoto, Y.; Tanaka, K., III; Morita, N.; Tamura, O. Org. Lett. 2021, 23, 1659.

  7. (a) Kumar, P.; Kapur, M. Org. Lett. 2020, 22, 5855. (b) Khasanov, A. F.; Kopchuk, D. S.; Nikonov, I. L.; Taniya, O. S.; Kovalev, I. S.; Zyryanov, G. V.; Rusinov, V. L.; Chupakhin, O. N. Russ. Chem. Bull. 2021, 70, 999.

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The study was supported by the Russian Science Foundation grant No. 22-13-00157, https://rscf.ru/project/22-13-00157.

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Correspondence to Saveliy P. Sorokin.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2022, 58(11), 582–584

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Sorokin, S.P., Ershov, O.V. The synthesis of ortho-stilbazoles (2-styrylpyridines) (microreview). Chem Heterocycl Comp 58, 582–584 (2022). https://doi.org/10.1007/s10593-022-03132-4

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  • DOI: https://doi.org/10.1007/s10593-022-03132-4