Chinese Journal of Organic Chemistry >
Recent Advances in Transition-Metal-Catalyzed C—H Activation of Pyridone/Isoquinolones
Received date: 2022-02-15
Revised date: 2022-03-29
Online published: 2022-04-22
Supported by
National Natural Science Foundation of China(21302064); Natural Science Foundation of Hubei Province(2017CFB690)
Pyridones/isoquinolones are a kind of important nitrogen-containing heterocyclic compounds, which have good biological activity and unique chemical properties, and play an important role in synthesis chemistry, functional materials, biomedicine and so on. Recently, transition-metal-catalyzed C—H activation has emerged as a more atom- and step-economi- cal strategy for the construction of functionalized pyridones/isoquinolones, and it has attracted the attention of many organic chemists. Herein, the recent advances in transition-metal-catalyzed C—H activation of pyridone/isoquinolone derivatives are summarized according to the types of metal catalysis. An emphasis on the discussion of catalytic system, reaction mechanisms, substrate scopes and synthetic applications is also introduced. Finally, the limitations and development trend of this research field are analyzed and prospected.
Key words： transition-metal-catalysis; pyridone; isoquinolone; C—H activation
Cheng Gong , Jian Tang , Fei Xu , Pengjie Li , Zetian Wang , Yumin Zhang , Guoxian Yu , Liang Wang . Recent Advances in Transition-Metal-Catalyzed C—H Activation of Pyridone/Isoquinolones[J]. Chinese Journal of Organic Chemistry, 2022 , 42(7) : 1925 -1949 . DOI: 10.6023/cjoc202202017
| [1] | (a) Zhang, M. F.; Lv, L. Z.; Li, K. J. Pharm. Pract. 2012, 30, 248. (in Chinese) |
| [1] | ( 张明峰, 吕志良, 李科, 药学实践杂志, 2012, 30, 248.) |
| [1] | (b) Jessen, H. J.; Gademann, K. Nat. Prod. Rep. 2010, 27, 1168. |
| [1] | (c) Mu, B.-S.; Zhang, Z.-H.; Wu, W.-B.; Yu, J.-S.; Zhou, J. Acta Chim. Sinica 2021, 79, 685. (in Chinese) |
| [1] | ( 穆博帅, 张志豪, 武文彪, 余金生, 周剑, 化学学报, 2021, 79, 685.) |
| [2] | Zhang, Y.; Pike, A. Bioorg. Med. Chem. Lett. 2021, 38, 127849. |
| [3] | Hibi, S.; Ueno, K.; Nagato, S.; Kawano, K.; Ito, K.; Norimine, Y.; Takenaka, O.; Hanada, T.; Yonaga, M. J. Med. Chem. 2012, 55, 10584. |
| [4] | (a) Pettit, G. R.; Ducki, S.; Eastham, S. A.; Melody, N. J. Nat. Prod. 2009, 72, 1279. |
| [4] | (b) Goodfellow, E.; Senhaji Mouhri, Z.; Williams, C.; Jean-Claude, B. J. Bioorg. Med. Chem. Lett. 2017, 27, 688. |
| [5] | Kaila, N.; Follows, B.; Leung, L.; Thomason, J.; Huang, A.; Moretto, A.; Janz, K.; Lowe, M.; Mansour, T. S.; Hubeau, C.; Page, K.; Morgan, P.; Fish, S.; Xu, X.; Williams, C.; Saiah, E. J. Med. Chem. 2014, 57, 1299. |
| [6] | (a) Dalton, T.; Faber, T.; Glorius, F. ACS Cent. Sci. 2021, 7, 245. |
| [6] | (b) Shabani, S.; Wu, Y.; Ryan, H. G.; Hutton, C. A. Chem. Soc. Rev. 2021, 50, 9278. |
| [6] | (c) Liu, B.; Romine, A. M.; Rubel, C. Z.; Engle, K. M.; Shi, B.-F. Chem. Rev. 2021, 121, 14957. |
| [6] | (d) Zhou, C.-N.; Zheng, Z.-A.; Chang, G.; Xiao, Y.-C.; Shen, Y.-H.; Li, G.; Zhang, Y.-M.; Peng, W.-M.; Wang, L.; Xiao, B. Curr. Org. Chem. 2019, 23, 103. |
| [6] | (e) Liao, G.; Wu, Y.-J.; Shi, B.-F. Acta Chim. Sinica 2020, 78, 289. (in Chinese) |
| [6] | ( 廖港, 吴勇杰, 史炳锋, 化学学报, 2020, 78, 289.) |
| [6] | (f) Li, C.-J. Chin. J. Chem. 2022, 40, 838. |
| [6] | (g) Wang, Z.-T.; Zheng, Z.-A.; Li, P.-J.; Zhou, C.-N.; Cai, S.-J.; Xiao, B.; Wang, L. Chin. J. Chem. 2021, 39, 2823. |
| [7] | (a) Biswas, A.; Maity, S.; Pan, S.; Samanta, R. Chem.-Asian J. 2020, 15, 2092. |
| [7] | (b) Hirano, K.; Miura, M. Chem. Sci. 2018, 9, 22. |
| [8] | (a) Gandeepan, P.; Müller, T.; Zell, D.; Cera, G.; Warratz, S.; Ackermann, L. Chem. Rev. 2019, 119, 2192. |
| [8] | (b) Liu, W.; Ackermann, L. ACS Catal. 2016, 6, 3743. |
| [8] | (c) Hu, Y.; Zhou, B.; Wang, C. Acc. Chem. Res. 2018, 51, 816. |
| [8] | (d) Aneeja, T.; Neetha, M.; Afsina, C. M. A.; Anilkumar, G. Catal. Sci. Technol. 2021, 11, 444. |
| [8] | (e) Son, J. Beilstein J. Org. Chem. 2021, 17, 1733. |
| [9] | Ni, J.; Zhao, H.; Zhang, A. Org. Lett. 2017, 19, 3159. |
| [10] | Wang, H.; Pesciaioli, F.; Oliveira, J. C. A.; Warratz, S.; Ackermann, L. Angew. Chem., Int. Ed. 2017, 56, 15063. |
| [11] | Chen, S. Y.; Han, X. L.; Wu, J. Q.; Li, Q.; Chen, Y.; Wang, H. Angew. Chem., Int. Ed. 2017, 56, 9939. |
| [12] | Kumar, A.; Muniraj, N.; Prabhu, K. R. Adv. Synth. Catal. 2019, 361, 4933. |
| [13] | Zheng, G.; Sun, J.; Xu, Y.; Zhai, S.; Li, X. Angew. Chem., Int. Ed. 2019, 58, 5090. |
| [14] | Zhu, C.; Kuniyil, R.; Ackermann, L. Angew. Chem., Int. Ed. 2019, 58, 5338. |
| [15] | Wan, S.; Luo, Z.; Xu, X.; Yu, H.; Li, J.; Pan, Y.; Zhang, X.; Xu, L.; Cao, R. Adv. Synth. Catal. 2021, 363, 2586. |
| [16] | Mohanty, S. R.; Prusty, N.; Banjare, S. K.; Nanda, T.; Ravikumar, P. C. Org. Lett. 2022, 24, 848. |
| [17] | Kong, L.; Yu,15, S.; Tang, G.; Wang, H.; Zhou, X.; Li, X. Org. Lett. 2016, 18, 3802. |
| [18] | Boerth, J. A.; Hummel, J. R.; Ellman, J. A. Angew. Chem., Int. Ed. 2016, 55, 12650. |
| [19] | Gao, F.; Han, X.; Li, C.; Liu, L.; Congae, Z.; Liu, H. RSC Adv. 2018, 8, 32659. |
| [20] | Zhu, C.; Kuniyil, R.; Jei, B. B.; Ackermann, L. ACS Catal. 2020, 10, 4444. |
| [21] | Wang, C. S.; Monaco, S. D.; Thai, A. N.; Rahman, M. S.; Pang, B. P.; Wang, C.; Yoshikai, N. J. Am. Chem. Soc. 2020, 142, 12878. |
| [22] | Mohanty, S. R.; Prusty, N.; Gupta, L.; Biswal, P.; Ravikumar, P. C. J. Org. Chem. 2021, 86, 9444. |
| [23] | (a) Nakao, Y.; Idei, H.; Kanyiva, K. S.; Hiyama, T. J. Am. Chem. Soc. 2009, 131, 15996. |
| [23] | (b) Tamura, R.; Yamada, Y.; Nakao, Y.; Hiyama, T. Angew. Chem., Int. Ed. 2012, 51, 5679. |
| [24] | Donets, P. A.; Cramer, N. Angew. Chem., Int. Ed. 2015, 54, 633. |
| [25] | Diesel, J.; Finogenova, A. M.; Cramer, N. J. Am. Chem. Soc. 2018, 140, 4489. |
| [26] | Miura, W.; Hirano, K.; Miura, M. J. Org. Chem. 2017, 82, 5337. |
| [27] | Shen, D.; Zhang, W. B.; Li, Z.; Shi, S. L.; Xu, Y. Adv. Synth. Catal. 2020, 362, 1125. |
| [28] | Yin, G.; Li, Y.; Wang, R. H.; Li, J. F.; Xu, X. T.; Luan, Y. X.; Ye, M. Acs. Catal. 2021, 11, 4606. |
| [29] | Peng, P.; Wang, J.; Li, C.; Zhu, W.; Jiang, H.; Liu, H. Rsc. Adv. 2016, 6, 57441. |
| [30] | Kumar, K. A.; Kannaboina, P.; Das, P. Org. Biomol. Chem. 2017, 15, 5457. |
| [31] | Zhang, L.; Zheng, X.; Chen, J.; Cheng, K.; Jin, L.; Jiang, X.; Yu, C. Org. Chem. Front. 2018, 5, 2969. |
| [32] | Fu, Y.; Wang, Z.; Zhang, Q.; Li, Z.; Liu, H.; Bi, X.; Wang, J. RSC Adv. 2020, 10, 6351. |
| [33] | Das, D.; Biswas, A.; Karmakar, U.; Chand, S.; Samanta, R. J. Org. Chem. 2016, 81, 842. |
| [34] | Peng, P.; Wang, J.; Jiang, H.; Liu, H. Org. Lett. 2016, 18, 5376. |
| [35] | Barday, M.; Janot, C.; Halcovitch, N. R.; Muir, J.; Aϊssa, C. Angew. Chem., Int. Ed. 2017, 56, 13117. |
| [36] | Xia, J.; Kong, L.; Zhou, X.; Zheng, G.; Li, X. Org. Lett. 2017, 19, 5972. |
| [37] | Hazra, S.; Hirano, K.; Miura, M. Asian J. Org. Chem. 2019, 8, 1097. |
| [38] | Zhao, H.; Xu, X.; Yu, H.; Li, B.; Xu, X.; Li, H.; Xu, L.; Fan, Q.; Walsh, P. J. Org. Lett. 2020, 22, 4228. |
| [39] | Tian, M.; Liu, B.; Sun, J.; Li, X. Org. Lett. 2018, 20, 4946. |
| [40] | Zhao, H.; Xu, X.; Luo, Z.; Cao, L.; Li, B.; Li, H.; Xu, L.; Fan, Q.; Walsh, P. J. Chem. Sci. 2019, 10, 10089. |
| [41] | Zhu, Y. Q.; Niu, Y. X.; Hui, L. W.; He, J. L.; Zhu, K. Adv. Synth. Catal. 2019, 361, 2897. |
| [42] | Yao, J.; Kong, L.; Li, X. Chem. Commun. 2020, 56, 13169. |
| [43] | Xu, X.; Luo, C.; Zhao, H.; Pan, Y.; Zhang, X.; Li, J.; Xu, L.; Lei, M.; Walsh, P. J. Chem.-Eur. J. 2021, 27, 8811. |
| [44] | Das, D.; Poddar, P.; Maity, S.; Samanta, R. J. Org. Chem. 2017, 82, 3612. |
| [45] | Grenet, E.; Das, A.; Caramenti, P.; Waser, J. Beilstein J. Org. Chem. 2018, 14, 1208. |
| [46] | Huang, G.; Shan, Y.; Yu, J. T.; Pan, C. Chem.-Eur. J. 2021, 27, 12294. |
| [47] | Yu, S.; Li, Y.; Zhou, X.; Wang, H.; Kong, L.; Li, X. Org. Lett. 2016, 18, 2812. |
| [48] | Li, T.; Wang, Z.; Xu, K.; Liu, W.; Zhang, X.; Mao, W.; Guo, Y.; Ge, X.; Pan, F. Org. Lett. 2016, 18, 1064. |
| [49] | Biswas, A.; Giri, D.; Das, D.; De, A.; Patra, S. K.; Samanta, R. J. Org. Chem. 2017, 82, 10989. |
| [50] | Li, J.; Yang, Y.; Wang, Z.; Feng, B.; You, J. Org. Lett. 2017, 19, 3083. |
| [51] | Zhou, X.; Pan, Y.; Li, X. Angew. Chem., Int. Ed. 2017, 56, 8163. |
| [52] | Zhou, C. J.; Gao, H.; Huang, S. L.; Zhang, S. S.; Wu, J. Q.; Li, B.; Jiang, X.; Wang, H. ACS Catal. 2019, 9, 556. |
| [53] | Li, Y.; Xie, F.; Li, X. J. Org. Chem. 2016, 81, 715. |
| [54] | Miura, W.; Hirano, K.; Miura, M. Org. Lett. 2016, 18, 3742. |
| [55] | Min, M.; Kang, D.; Jung, S.; Hong, S. Adv. Synth. Catal. 2016, 358, 1296. |
| [56] | Cui, Y.; Bai, D.; Liu, B.; Chang, J.; Li, X. Chem. Commun. 2020, 56, 15631. |
| [57] | Hazra, S.; Hirano, K.; Miura, M. Heterocycles 2020, 101, 223. |
| [58] | Itahara, T.; Ouseto, F. Synthesis 1984, 16, 488. |
| [59] | (a) Cheng, D.; Gallagher, T. Org. Lett. 2009, 11, 2639. |
| [59] | (b) Chen, Y.; Wang, F.; Jia, A.; Li, X. Chem. Sci. 2012, 3, 3231. |
| [59] | (c) Anagnostaki, E. E.; Fotiadou, A. D.; Demertzidou, V.; Zografos, A. L. Chem. Commun. 2014, 50, 6879. |
| [59] | (d) Lah, H. U.; Rasool, F.; Yousuf, S. K. RSC Adv. 2015, 5, 78958. |
| [60] | Maity, S.; Das, D.; Sarkar, S.; Samanta, R. Org. Lett. 2018, 20, 5167. |
| [61] | Katsina, T.; Papoulidou, K. E.; Zografos, A. L. Org. Lett. 2019, 21, 8110. |
| [62] | Miura, W.; Hirano, K.; Miura, M. Synthesis 2017, 49, 4745. |
| [63] | Dasa, D.; Samanta, R. Adv. Synth. Catal. 2018, 360, 379. |
/
| 〈 |
|
〉 |
