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Chinese Journal of Organic Chemistry >

2022 , Vol. 42 >Issue 5: 1396 - 1406

DOI: https://doi.org/10.6023/cjoc202201025

ARTICLES

Photoredox Catalytic Cascade Radical Addition to Construct 1,4- Diketone-Functionalized Quinoxalin-2(1H)-one Derivatives

  • Xin Sun ,
  • Chaofan Qu ,
  • Chaorui Ma ,
  • Xiaowei Zhao ,
  • Guobi Chai ,
  • Zhiyong Jiang
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  • a International Scientific and Technological Cooperation Base of Chiral Chemistry, Henan University, Kaifeng, Henan 475004
    b School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007
    c Key Laboratory of Tobacco Flavor Basic Research of China National Tobacco Corporation, Zhengzhou Tobacco Research Institute of China National Tobacco Corporation, Zhengzhou 450001
†These authors contributed equally to this work.
*Corresponding authors. E-mail: ;

Received date: 2022-01-17

  Revised date: 2022-01-26

  Online published: 2022-01-28

Supported by

National Natural Science Foundation of China(21925103); Young Elite Scientists Sponsorship Program by China Association for Science and Technology(2017QNRC001)

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Abstract

The biological importance of quinoxalin-2(1H)-ones has inspired increasing pursuit for the development of efficient and expedient synthetic methods to access these entities. Among them, C3—H functionalization of quinoxalin-2(1H)- ones has been a sought-after strategy in recent years, especially using photocatalysis platform to trigger radical intermediates. Besides the direct addition of photocatalysis-yielding radicals to 3-position of quinoxalin-2(1H)-ones, a handful of three- component cascade reactions have been described, wherein olefins were used to preferentially accept radicals to generate new radical intermediates to experience the second addition process. Given the robust ability of cascade strategy to enrich the varieties of quinoxalin-2(1H)-ones, the exploration of new protocols remains a highly attractive task. Herein, we report photoredox catalytic reactions of quinoxalin-2(1H)-ones with 2-bromo-1-arylethan-1-ones as the partners, leading to a series of valuable 1,4-diketone-functionalized quinoxalin-2(1H)-one derivatives with satisfactory results. This is an unprecedented cascade reaction strategy, involving radical addition to quinoxalin-2(1H)-ones and the resultant intermediates to accept a second addition of radicals generated from bromide substrates or to experience SN2 reaction with bromides.

Key words： visible light; photoredox catalysis; radical addition; cascade reaction; quinoxalin-2(1H)-ones

Cite this article

Xin Sun , Chaofan Qu , Chaorui Ma , Xiaowei Zhao , Guobi Chai , Zhiyong Jiang . Photoredox Catalytic Cascade Radical Addition to Construct 1,4- Diketone-Functionalized Quinoxalin-2(1H)-one Derivatives[J]. Chinese Journal of Organic Chemistry, 2022 , 42(5) : 1396 -1406 . DOI: 10.6023/cjoc202201025

References

[1]
(a) Shi, L.-L.; Zhou, H.; Wu, J.-F.; Li, X. Mini-Rev. Org. Chem. 2015, 12, 96.
[1]
(b) Carta, A.; Piras, S.; Loriga, G.; Paglietti, G. Mini-Rev. Med. Chem. 2006, 6, 1179.
[1]
(c) Li, X.; Yang, K.; Li, W.; Xu, W. Drugs Future 2006, 31, 979.
[1]
(d) Akins, P. T.; Atkinson, R. P. Curr. Med. Res. Opin. 2002, 18, 9.
[2]
For selected reviews, see: (a) Ke, Q.; Yan, G.; Yu, J.; Wu, X. Org. Biomol. Chem. 2019, 17, 5863.
[2]
(b) Monika, M.; Selvakumar, S. Synthesis 2019, 4113.
[2]
(c) Ghosh, P.; Das, S. Synth. Commun. 2020, 50, 2266.
[2]
(d) Meng, W.; Xu, K.; Guo, B.; Zeng, C. Chin. J. Org. Chem. 2021, 41, 2621. (in Chinese)
[2]
(孟薇, 徐坤, 郭兵冰, 曾程初, 有机化学, 2021, 41, 2621.)
[2]
(e) Liu, X.; Li, W.; Zhuang, C.; Cao, H. Chin. J. Org. Chem. 2021, 41, 3459. (in Chinese)
[2]
(刘想, 李文, 庄灿展, 曹华, 有机化学, 2021, 41, 3459.)
[2]
(f) Li, D.; Wang, X.; Li, S.; Fu, C.; Li, Q.; Xu, D.; Ma, Y. Chin. J. Org. Chem. 2021, 41, 4610. (in Chinese)
[2]
(李丹丹, 王晓辰, 李闪闪, 付晨雨, 李倩倩, 许东涛, 马莹莹, 有机化学, 2021, 41, 4610.)
[3]
For selected recent examples of direct functionalization except of photocatalytic reactions, see: (a) Liu, S.; Huang, Y.; Qing, F.-L.; Xu, X.-H. Org. Lett. 2018, 20, 5497.
[3]
(b) Dutta, H. S.; Ahmad, A.; Khan, A. A.; Kumar, M.; Raziullah; Koley, D. Adv. Synth. Catal. 2019, 361, 5534.
[3]
(c) Zheng, D.; Studer, A. Org. Lett. 2019, 21, 325.
[3]
(d) Shen, J.; Xu, J.; Huang, L.; Zhu, Q.; Zhang, P. Adv. Synth. Catal. 2020, 362, 230.
[3]
(e) Lu, J.; He, X.-K.; Cheng, X.; Zhang, A.-J.; Xu, G.-Y.; Xuan, J. Adv. Synth. Catal. 2020, 362, 2178.
[3]
(f) Su, H.-Y.; Zhu, X.-L.; Huang, Y.; Xu, X.-H.; Qing, F.-L. Chem. Commun. 2020, 56, 12805.
[3]
(g) Wang, J.; Sun, B.; Zhang, L.; Xu, T.; Xie, Y.; Jin, C. Org. Chem. Front. 2020, 7, 113.
[3]
(h) Yuan, J.-W.; Zhu, J.-L.; Zhu, H.-L.; Peng, F.; Yang, L.-Y.; Mao, P.; Zhang, S.-R.; Li, Y.-C.; Qu, L.-B. Org. Chem. Front. 2020, 7, 273.
[3]
(i) Xu, J.; Zhang, H.; Zhao, J.; Ni, Z.; Zhang, P.; Shi, B.-F.; Li, W. Org. Chem. Front. 2020, 7, 4031.
[3]
(j) Meng, N.; Wang, L.; Liu, Q.; Li, Q.; Lv, Y.; Yue, H.; Wang, X.; Wei, W. J. Org. Chem. 2020, 85, 6888.
[3]
(k) Xu, J.; Yang, H.; He, L.; Huang, L.; Shen, J.; Li, W.; Zhang, P. Org. Lett. 2021, 23, 195.
[3]
(l) Wen, J.; Yang, X.; Yan, K.; Qin, H.; Ma, J.; Sun, X.; Yang, J.; Wang, H. Org. Lett. 2021, 23, 1081.
[3]
(m) He, X.-K.; Lu, J.; Zhang, A.-J.; Zhang, Q.-Q.; Xu, G.-Y.; Xuan, J. Org. Lett. 2020, 22, 5984.
[3]
(n) Niu, K.; Song, L.; Hao, Y.; Liu, Y.; Wang, Q. Chem. Commun. 2020, 56, 11673.
[3]
(o) Clinton, C. D.; Prasad, C. D.; Thombal, R. S.; Lee, Y. R. Adv. Synth. Catal. 2021, 363, 776.
[4]
For a review on photocatalytic functionalization, see: (a) Rostoll-Berenguer, J.; Blay, G.; Pedro, J. R.; Vila, C. Eur. J. Org. Chem. 2020, 6148.
[5]
(a) Bao, P.; Liu, F.; Lv, Y.; Yue, H.; Li, J.-S.; Wei, W. Org. Chem. Front. 2020, 7, 492.
[5]
(b) Dai, C.; Zhan, Y.; Liu, P.; Sun, P. Green Chem. 2021, 23, 314.
[5]
(c) Aganda, K. C. C.; Hong, B.; Lee, A. Adv. Synth. Catal. 2021, 363, 1443.
[6]
(a) Meng, N.; Lv, Y.; Liu, Q.; Liu, R.; Zhao, X.; Wei, W. Chin. Chem. Lett. 2021, 32, 258.
[6]
(b) Yang, X.; Meng, W.-D.; Xu, X.-H.; Huang, Y. Org. Chem. Front. 2021, 8, 6597.
[7]
For selected reviews, see: (a) Lv, X.; Xu, H.; Yin, Y.; Zhao, X.; Jiang, Z. Chin. J. Chem. 2020, 38, 1480.
[7]
(b) Yin, Y.; Zhao, X.; Qiao, B.; Jiang, Z. Org. Chem. Front. 2020, 7, 1283.
[7]
(c) Yin, Y.; Zhao, X.; Jiang, Z. ChemCatChem 2020, 12, 4471.
[7]
For selected examples see: (d) Shao, T.; Yin, Y.; Lee, R.; Zhao, X.; Chai, G.; Jiang, Z. Adv. Synth. Catal. 2018, 360, 1754.
[7]
(e) Li, J.; Gu, Z.; Zhao, X.; Qiao, B.; Jiang, Z. Chem. Commun. 2019, 55, 12916.
[7]
(f) Qiao, B.; Li, C.; Zhao, X.; Yin, Y.; Jiang, Z. Chem. Commun. 2019, 55, 7534.
[7]
(g) Yin, Y.; Dai, Y.; Jia, H.; Li, J.; Bu, L.; Qiao, B.; Zhao, X.; Jiang, Z. J. Am. Chem. Soc. 2018, 140, 6083.
[7]
(h) Cao, K.; Tan, S. M.; Lee, R.; Yang, S.; Jia, H.; Zhao, X.; Qiao, B.; Jiang, Z. J. Am. Chem. Soc. 2019, 141, 5437.
[7]
(i) Yin, Y.; Li, Y.; Gonçalves, T. P.; Zhan, Q.; Wang, G.; Zhao, X.; Qiao, B.; Huang, K.-W.; Jiang, Z. J. Am. Chem. Soc. 2020, 142, 19451.
[7]
(j) Kong, M.; Tan, Y.; Zhao, X.; Qiao, B.; Tan, C.-H.; Cao, S.; Jiang, Z. J. Am. Chem. Soc. 2021, 143, 4024.
[7]
(k) Guo, Z.; Chen, X.; Fang, H.; Zhao, X.; Jiang, Z. Sci. China Chem. 2021, 64, 1522.
[7]
(l) Hu, W.; Zhan, Q.; Zhou, H.; Cao, S.; Jiang, Z. Chem. Sci. 2021, 12, 6543.
[7]
(m) Chen, X.; Wei, W.; Li, C.; Zhou, H.; Qiao, B.; Jiang, Z. Org. Lett. 2021, 23, 8744.
[7]
(n) Chai, X.; Hu, X.; Zhao, X.; Yin, Y.; Cao, S.; Jiang, Z. Angew. Chem. Int. Ed. 2022, 61, e202115110.
[7]
(o) Tan, Y.; Yin, Y.; Cao, S.; Zhao, X.; Qu, G.; Jiang, Z. Chin. J. Catal. 2022, 43, 558.
[8]
(a) Zhao, Y.; Zhang, C.; Chin, K. F.; Pytela, O.; Wei, G.; Liu, H.; Bureš, F.; Jiang, Z. RSC Adv. 2014, 4, 30062.
[8]
(b) Liu, X.; Ye, X.; Bureš, F.; Liu, H.; Jiang, Z. Angew. Chem. Int. Ed. 2015, 54, 11443.
[8]
(c) Shao, T.; Jiang, Z. Acta Chim. Sinica 2017, 75, 70. (in Chinese)
[8]
(邵天举, 江智勇, 化学学报, 2017, 75, 70.)
[8]
(d) Jia, H.; Qiao, B.; Jiang, Z. Acta Chim. Sinica 2021, 79, 1477. (in Chinese)
[8]
(贾红绍, 乔保坤, 江智勇, 化学学报, 2021, 79, 1477.)
[8]
(e) Yang, H.; Li, H.; Wei, G.; Jiang, Z. Angew. Chem. Int. Ed. 2021, 60, 19696.
[9]
Badawy, M. A.; Mohamed, G. G.; Omar, M. M.; Nassar, M. M.; Kamel, A. B. Eur. J. Chem. 2010, 4, 282.
[10]
See the Supporting Information for the details.
[11]
Li, J.; Kong, M.; Qiao, B.; Lee, R.; Zhao, X.; Jiang, Z. Nat. Commun. 2018, 9, 2445.
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