光/电化学合成在喹喔啉-2(1H)-酮C—H键官能化中的应用
收稿日期: 2021-03-19
修回日期: 2021-04-04
网络出版日期: 2021-06-08
基金资助
国家自然科学基金(22001045); 广东省创新强校项目(2019KQNCX061); 省市共建重点学科建设专项资助项目.
Application of Photochemical/Electrochemical Synthesis in C—H Functionalization of Quinoxalin-2(1H)-one
Received date: 2021-03-19
Revised date: 2021-04-04
Online published: 2021-06-08
Supported by
National Natural Science Foundation of China(22001045); Innovation and Strong School Project of Guangdong Pharmaceutcal University(2019KQNCX061); Special Funds of Key Disciplines Construction from Guangdong and Zhongshan Cooperating.
喹喔啉-2(1H)-酮是一类重要的含氮杂环化合物, 具有很强的生物活性与化学特性, 在合成化学、功能材料及药物工业等方面具有重要应用. 近年来, 通过C—H官能化构建3-官能化的喹喔啉-2(1H)-酮引起了很多学者的关注, 并取得了重要进展. 其中, 基于绿色化学导向的光催化及电化学合成正成为喹喔啉-2(1H)-酮的C—H官能化的强有力工具. 鉴于光电化学在合成化学中的巨大影响, 总结了可见光催化与电化学合成实现喹喔啉-2(1H)-酮3位C—H官能化的研究现状, 希望能促进绿色合成策略在含氮杂环官能化中的进一步发展.
关键词： 喹喔啉-2(1H)-酮; 可见光; 电化学; C—H官能化
刘想 , 李文 , 庄灿展 , 曹华 . 光/电化学合成在喹喔啉-2(1H)-酮C—H键官能化中的应用[J]. 有机化学, 2021 , 41(9) : 3459 -3481 . DOI: 10.6023/cjoc202103032
Quinoxalin-2(1H)-ones are a kind of important nitrogen-containing heterocyclic compounds, which have strong biological activity and chemical properties, and play an important role in synthesis chemistry, functional materials, drugs and so on. In recent years, the construction of 3-functionalized quinoxalin-2(1H)-one by C—H functionalization has attracted the attention of many scholars and made important progress. Among them, green chemistry oriented photocatalysis and electrochemical synthesis are becoming powerful tools for C—H functionalization of quinoxaline-2(1H)-one. In view of the great influence of photochemistry in synthetic chemistry, the research status of C—H functionalization of quinoxaline- 2(1H)-one in visible light catalysis and electrochemical synthesis is summarized, hoping to promote the further development of green synthesis strategy in the functionalization of nitrogen-containing heterocycles.
| [1] | Yang, Y. C.; Zhang, S. Z.; Wu, B. B.; Ma, M. M.; Chen, X.; Qin, X. Y.; He, M. L.; Hussain, S.; Jing, C. J.; Ma, B.; Zhu, C. ChemMedChem 2012, 7, 823. |
| [1] | (b) Shi, L. L.; Hu, W.; Wu, J. F.; Zhou, H. Y.; Zhou, H.; Li, L. Mini-Rev. Med. Chem. 2018, 18, 392. |
| [1] | (c) Hussain, S.; Parveen, S.; Hao, X.; Zhang, S. Z.; Wang, W.; Qin, X. Y.; Yang, Y. C.; Chen, X.; Zhu, S. J.; Zhu, C. J.; Ma, B. Eur. J. Med. Chem. 2014, 80, 383. |
| [1] | (d) Shi, J. W.; Wei, W. Chin. J. Org. Chem. 2020, 40, 2170. (in Chinese). |
| [1] | ( 时建伟, 魏伟, 有机化学, 2020, 40, 2170.) |
| [1] | (e) Mao, P.; Zhu, J. L.; Yuan, J. W.; Liang, L. R.; Xiao, Y. M.; Zhang, C. S. Chin. J. Org. Chem. 2019, 39, 1529. (in Chinese). |
| [1] | ( 毛璞, 朱军亮, 袁金伟, 杨亮茹, 肖咏梅, 张长森, 有机化学, 2019, 39, 1529.) |
| [1] | (f) Hai, M.; Guo, L. N.; Wang, L.; Duan, X. H. Acta. Chim. Sinica 2019, 77, 895. (in Chinese). |
| [1] | ( 海曼, 郭丽娜, 王乐, 段新华, 化学学报, 2019, 77, 895.) |
| [2] | (a) Weïwer, M.; Spoonamore, J.; Wei, J.; Guichard, B.; Ross, N. T.; Masson, K.; Silkworth, W.; Dandapani, S.; Palmer, M.; Scherer, C. A.; Stern, A. M.; Schreiber, S. L.; Munoz, B. ACS Med. Chem. Lett. 2012, 3, 1034. |
| [2] | (b) Qin, X. Y.; Hao, X.; Han, H.; Zhu, S. J.; Yang, Y. C.; Wu, B. B.; Hussain, S.; Parveen, S.; Jing, C. J.; Ma, B.; Zhu, C. J. J. Med. Chem. 2015, 58, 1254. |
| [2] | (c) Ajani, O. O. Eur. J. Med. Chem. 2014, 85, 688. |
| [2] | (d) Lawrence, D. S.; Copper, J. E.; Smith, C. D. J. Med. Chem. 2001, 44, 594. |
| [2] | (e) Liu, Z.; Yu, S.; Chen, D.; Shen, G.; Wang, Y.; Hou, L.; Lin, D.; Zhang, J.; Ye, F. Drug Des., Dev. Ther. 2016, 10, 1489. |
| [3] | (a) Qin, Y.; Zhu, L.; Luo, S. Chem. Rev. 2017, 117, 9433. |
| [3] | (b) Ping, L.; Chung, D. S.; Bouffard, J.; Lee, S. G. Chem. Soc. Rev. 2017, 46, 4299. |
| [3] | (c) Shen, J. B.; Xu, J.; Huang, L.; Zhu, Q.; Zhang, P. F. Adv. Synth. Catal. 2020, 362, 230. |
| [3] | (d) Yuan, J. W.; Liu, S. N.; Qiao, L. B. Adv. Synth. Catal. 2017, 359, 4197. |
| [3] | (e) Ramesh, B.; Reddy, C. R.; Kumar, G. R.; Reddy, B. V. S. Tetrahedron Lett. 2018, 59, 628. |
| [3] | (f) Aganda, K. C. C.; Hong, B.; Lee, A. Adv. Synth. Catal. 2021, 363, 1443. |
| [4] | (a) Yuan, J. W.; Fu, J. H.; Yin, J. H.; Dong, Z. H.; Xiao, Y. M.; Mao, P.; Qu, L. B. Org. Chem. Front. 2018, 5, 2820. |
| [4] | (b) Wang, L. P.; Zhang, Y. C.; Li, F. F.; Hao, X. Y.; Zhang, H. Y.; Zhao, J. Q. Adv. Synth. Catal. 2018, 360, 3969. |
| [4] | (c) Hong, G. F.; Yuan, J. W.; Fu, J. H.; Pan, G. Y.; Wang, Z. W.; Yang, L. R.; Xiao, Y. M.; Mao, P.; Zhang, X. M. Org. Chem. Front. 2019, 6, 1173. |
| [4] | (d) Wang, J.; Li, J.; Wei, Y. Y.; Yang, J. Y.; Huo, C. D. Org. Chem. Front. 2018, 5, 3534. |
| [4] | (e) Ke, Q. M.; Yan, G. B.; Yu, J.; Wu, X. M. Org. Biomol. Chem. 2019, 17, 5863. |
| [5] | (a) He, K. H.; Tan, F. F.; Zhou, C. Z.; Zhou, G. J.; Yang, X. L.; Li, Y. Angew. Chem., nt. Ed. 2017, 56, 3080. |
| [5] | (b) Wang, H. M.; Gao, X. L.; Lv, Z. C.; Abdelilah, T.; Lei, A. W. Chem. Rev. 2019, 119, 6769. |
| [5] | (c) Yu, X. Y.; Chen, J. R.; Xiao, W. J. Chem. Rev. 2021, 121, 506. |
| [5] | (d) Mcatee, R. C.; Mcclain, E. J.; Stephenson, C. R. J. Trends Chem. 2019, 1, 111. |
| [5] | (d) Bhaskaran, R. P.; Babu, B. P. Adv. Synth. Catal. 2020, 362, 5219. |
| [5] | (e) Pan, X. L.; Xia, H. G.; Wu, J. Org. Chem. Front. 2016, 3, 1163. |
| [5] | (f) Shen, J. B.; Xu, J.; He, L.; Ouyang, Y.; Haung, L.; Li, W. M.; Zhu, Q.; Zhang, P. F. Org. Lett. 2021, 23, 1204. |
| [5] | (g) Xu, J.; Huang, L.; He, L.; Ni, Z. G.; Shen, J. B.; Li, X. L.; Chen, K. X.; Li, W. M.; Zhang, P. F. Green Chem. 2021, 23, 2123. |
| [6] | (a) Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev. 2013, 7, 5322. |
| [6] | (b) Romero, N. A.; Nicewicz, D. A. Chem. Rev. 2016, 17, 10075. |
| [6] | (c) Hari, D. P.; König, B. Chem. Commun. 2014, 50, 6688. |
| [7] | (a) Jiang, Y. Y.; Xu, K.; Zeng, C. C. Chem. Rev. 2018, 9, 4485. |
| [7] | (b) Waldvogel, S. R.; Lips, S.; Selt, M.; Riehl, B.; Kampf, C. J. Chem. Rev. 2018, 118, 6706. |
| [7] | (c) Pegis, M. L.; Wise, C. F.; Martin, D. J.; Mayer, J. M. Chem. Rev. 2018, 5, 2340. |
| [7] | (d) Wang, H. Q.; Xu, W. T.; Xin, L. L.; Liu, W. M.; Wang, Z. Q.; Xu, K. J. Org. Chem. 2016, 81, 3681. |
| [8] | (a) Cui, Z. M.; Zhu, B. F.; Li, X. C.; Cao, H. Org. Chem. Front. 2018, 5, 2219. |
| [8] | (b) Yu, Y.; Su, Z. Q.; Cao, H. Chem. Rec. 2019, 19, 2105. |
| [8] | (c) Cao, H.; Lei, S.; Li, N. Y.; Chen, L. B.; Liu, J. Y.; Cai, H. Y.; Qiu, S. X.; Tan, J. W. Chem. Commun. 2015, 51, 1823 |
| [8] | (d) Lei, S.; Cao, H.; Chen, L. B.; Liu, J. Y.; Cai, H. Y. Adv. Synth. Catal. 2015, 357, 3109. |
| [9] | (a) Brahmachari, G. RSC Adv. 2016, 6, 64676. |
| [9] | (b) Resch, V.; Schrittwieser, J. H.; Siirola, E.; Kroutil, W. Curr. Opin. Biotechnol. 2011, 22, 793. |
| [9] | (c) Yamaguchi, J.; Yamaguchi, A. D.; Itami, K. Angew. Chem., Int. Ed. 2012, 51, 8960. |
| [10] | Wei, W.; Wang, L. L.; Yue, H. L.; Bao, P. L.; Liu, W. W.; Hu, C. S.; Yang, D. S.; Wang, H. ACS Sustainable Chem. Eng. 2018, 6, 17252. |
| [11] | Zhang, W.; Pan, Y. L.; Yang, C.; Chen, L.; Li, X.; Cheng, J. P. J. Org. Chem. 2019, 84, 7786. |
| [12] | Zhang, W.; Pan, Y. L.; Yang, C.; Li, X.; Wang, B. Org. Chem. Front. 2019, 6, 2765. |
| [13] | Zhao, B.; Kong, X. Q.; Xu, B. Tetrahedron Lett. 2019, 60, 2063. |
| [14] | Zhang, H. D.; Xu, J.; Zhao, J. M.; Zhang, P. F.; Li, W. M. Org. Biomol. Chem. 2019, 17, 10201. |
| [15] | Liu, L. X.; Pan, N.; Sheng, W.; Su, L. B.; Liu, L.; Dong, J. Y.; Zhou, Y. B.; Yin, S. F. Adv. Synth. Catal. 2019, 361, 4126. |
| [16] | Yan, Z. Y.; Sun, B.; Zhang, X.; Zhuang, X. H.; Yang, J.; Su, W. K.; Jin, C. Chem.-Asian J. 2019, 14, 3344. |
| [17] | Xue, W. X.; Su, Y. P.; Wang, K. H.; Zhang, R.; Feng, Y. W.; Cao, L. D.; Huang, D. F.; Hu, Y. L. Org. Biomol. Chem. 2019, 17, 6654. |
| [18] | Xie, L. Y.; Jiang, L. L.; Tan, J. X.; Wang, Y.; Xu, X. Q.; Zhang, B.; Cao, Z.; He, W. M. ACS Sustainable Chem. Eng. 2019, 7, 14153. |
| [19] | Mane, K. D.; Kamble, R. B.; Suryavanshi, G. New J. Chem. 2019, 43, 7403. |
| [20] | Wei, Z. J.; Qi, S. J.; Xu, Y. H.; Liu, H.; Wu, J. Z.; Li, H. S.; Xia, C. C.; Duan, G. Y. Adv. Synth. Catal. 2019, 361, 5490. |
| [21] | Zheng, D. Q.; Studer, A. Org. Lett. 2019, 21, 325. |
| [22] | Wang, J. Y.; Sun, B.; Zhang, L.; Xu, T. W.; Xie, Y. Y.; Jin, C. Asian J. Org. Chem. 2019, 8, 1942. |
| [23] | Jin, C.; Zhuang, X. C.; Sun, B.; Li, D. Y.; Zhu, R. Asian J. Org. Chem. 2019, 8, 1490. |
| [24] | He, X. K.; Lu, J.; Zhang, A. J.; Zhang, Q. Q.; Xu, G. Y.; Xuan, J. Org. Lett. 2020, 22, 5984. |
| [25] | Zhang, W.; Xiang, X. X.; Chen, J. Y.; Yang, C.; Pan, Y. L.; Cheng, J. P.; Meng, J. B.; Li, X. Nat. Commun. 2020, 11, 638. |
| [26] | Gao, Y. H.; Zhao, L. L.; Xiang, T. Y.; Li, P. H.; Wang, L. RSC Adv. 2020, 10, 10559. |
| [27] | Wang, L. L.; Bao, P. L.; Liu, W. W.; Liu, S. T.; Hu, C. S.; Yue, H. L.; Yang, D. S.; Wei, W. Chin. J. Org. Chem. 2018, 38, 3189. (in Chinese). |
| [27] | ( 王雷雷, 鲍鹏丽, 刘维伟, 刘思彤, 胡昌松, 岳会兰, 杨道山, 魏伟, 有机化学, 2018, 38, 3189.) |
| [28] | Kwon, S. J.; Jung, H. I.; Kim, D. Y. ChemistrySelect 2018, 3, 5824. |
| [29] | Bao, P. L.; Liu, F.; Lv, Y. F.; Yue, H. L.; Li, J. S.; Wei, W. Org. Chem. Front. 2019, 2020, 492. |
| [30] | Xie, L. Y.; Bai, Y. S.; Xu, X. Q.; Xia, P.; Tang, H. S.; Huang, Y.; Lin, Y. W.; Cao, Z.; He, W. M. Green Chem. 2020, 22, 1720. |
| [31] | Lu, J.; He, X. K.; Cheng, X.; Zhang, A.; Xu, G. Y.; Xuan, J. Adv. Synth. Catal. 2020, 362, 2179. |
| [32] | Xie, L.Y.; Peng, S.; Peng, L. H.; Peng, C.; Lin, Y. W.; Yu, X. Y.; Cao, Z.; Peng, Y. Y.; He, W. M. Green Chem. 2021, 23, 374. |
| [33] | Wei, W.; Wang, L. L.; Bao, P. L.; Shao, Y.; Yue, H. L.; Yang, D. S.; Yang, X. B.; Zhao, X. H.; Wang, H. Org. Lett. 2018, 20, 7125. |
| [34] | Xie, L. Y.; Hu, J. L.; Song, Y. X.; Jia, G. K.; Lin, Y. W.; He, J. Y.; Cao, Z.; He, W. M. ACS Sustainable Chem. Eng. 2019, 7, 19993. |
| [35] | Sun, M. L.; Wang, L.; Zhao, L. L.; Wang, Z. M.; Li, P. H. ChemCatChem 2020, 12, 5261. |
| [36] | Zhao, L. L.; Wang, L.; Gao, Y. H.; Wang, Z. M.; Li, P. H. Adv. Synth. Catal. 2019, 361, 1. |
| [37] | Zhou, J. D.; Zhou, P.; Zhao, T. T.; Ren, Q. L.; Li, J. J. Adv. Synth. Catal. 2019, 361, 5371. |
| [38] | Xu, X. B.; Xia, C. C.; Li, X. J.; Sun, J.; Hao, L. Q. RSC Adv. 2020, 10, 2016. |
| [39] | Xie, L. Y.; Liu, Y. S.; Ding, H. R.; Gong, S.; Tan, J. X.; He, J. Y.; Gao, Z.; He, W. M. Chin. J. Catal. 2020, 41, 1168. |
| [40] | Teng, Q. H.; Yao, Y.; Wei, W. X.; Tang, H. T.; Li, J. R.; Pan, Y. M. Green Chem. 2019, 21, 6241. |
| [41] | Xie, L. Y.; Chen, Y. L.; Qin, L.; Wen, Y.; Xie, J. W.; Tan, J. X.; Huang, Y.; Cao, Z.; He, W. M. Org. Chem. Front. 2019, 6, 3950. |
| [42] | Kim, Y.; Kim, D. Y. Tetrahedron Lett. 2018, 59, 2443. |
| [43] | Dai, C. H.; Zhan, Y. L.; Liu, P.; Sun, P. P. Green Chem. 2021, 23, 314. |
| [44] | Dou, G. Y.; Jiang, Y. Y.; Xu, K.; Zeng, C. C. Org. Chem. Front. 2019, 6, 2392. |
| [45] | Niu, K. K.; Song, L. Y.; Hao, Y. K.; Wang, Q. M. Chem. Commun. 2020, 56, 11673. |
| [46] | Gao, Y. Y.; Wu, Z. G.; Yu, L.; Wang, Y.; Pan, Y. Angew. Chem., Int. Ed. 2020, 59, 10859. |
| [47] | Wen, J. W.; Yang, X. T.; Yan, K. L.; Qin, H. Y.; Ma, J.; Sun, X. J.; Yang, J. J.; Wang, H. Org. Lett. 2021, 23, 1081. |
| [48] | Niu, K. K.; Hao, Y. K.; Song, L. Y.; Liu, Y. X.; Wang, Q. M. Green Chem. 2021, 23, 302. |
| [49] | Li, K. J.; Xu, K.; Liu, Y. G.; Zeng, C. C.; Sun, B. G. Adv. Synth. Catal. 2018, 361, 1033. |
| [50] | Jiang, X. P.; Yang, L. C.; Ye, Z. H.; Du, X. F.; Fang, L. Y.; Zhu, Y.; Chen, K. D.; Li, J. J.; Yu, C. M. Eur. J. Org. Chem. 2020, 2020, 1687. |
| [51] | Zhou, J. D.; Li, Z. H.; Sun, Z. X.; Ren, Q. L.; Zhang, Q. W.; Li, H.; Li, J. J. J. Org. Chem. 2020, 85, 4365. |
| [52] | Li, K. J.; Jiang, Y. Y.; Xu, K.; Zeng, C. C.; Sun, B. G. Green Chem. 2019, 21, 4412. |
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