Visible-light-initiated 4CzIPN catalyzed multi-component tandem reactions to assemble sulfonated quinoxalin-2(1H)-ones
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* Corresponding author.
E-mail address: weiweiqfnu@163.com (W. Wei).
Citation: Zhiwei Wang, Qishun Liu, Ruisheng Liu, Zhongyin Ji, Yan Li, Xiaohui Zhao, Wei Wei. Visible-light-initiated 4CzIPN catalyzed multi-component tandem reactions to assemble sulfonated quinoxalin-2(1H)-ones[J]. Chinese Chemical Letters, ;2022, 33(3): 1479-1482. doi: 10.1016/j.cclet.2021.08.036
N. Udilova, A.V. Kozlov, W. Bieberschulte, et al., Biochem. Pharmacol. 65(2003) 59-65.
doi: 10.1016/S0006-2952(02)01452-1
H. Nohl, W. Bieberschulte, B. Dietrich, N. Udilova, A.V. Kozlov, J. Heterocycl. Chem. 43(2006) 541-548.
doi: 10.1002/jhet.5570430304
Q. Ke, G. Yan, J. Yu, X. Wu, Org. Biomol. Chem. 17(2019) 5863-5881.
doi: 10.1039/C9OB00782B
J. Yuan, S. Liu, Y. Xiao, et al., Org. Biomol. Chem. 17(2019) 876-884.
doi: 10.1039/C8OB03061H
Y. Li, M. Gao, L. Wang, X. Cui, Org. Biomol. Chem. 14(2016) 8428-8432.
doi: 10.1039/C6OB01283C
W. Wei, L. Wang, P. Bao, et al., Org. Lett. 20(2018) 7125-7130.
doi: 10.1021/acs.orglett.8b03079
J.W. Yuan, J.H. Fu, S.N. Liu, et al., Org. Biomol. Chem. 16(2018) 3203-3212.
doi: 10.1039/C8OB00206A
L.Y. Xie, S. Peng, T.G. Fan, et al., Sci. China Chem. 62(2019) 460-464.
doi: 10.1007/s11426-018-9446-1
P. Bao, F. Liu, Y. Lv, et al., Org. Chem. Front. 7(2020) 492-498.
doi: 10.1039/C9QO01334B
L.Y. Xie, Y.S. Bai, X.Q. Xu, et al., Green Chem. 22(2020) 1720-1725.
doi: 10.1039/C9GC03899J
J. Yuan, J. Fu, J. Yin, et al., Org. Chem. Front. 5(2018) 2820-2828.
doi: 10.1039/C8QO00731D
W. Wei, L. Wang, H. Yue, et al., ACS Sustain. Chem. Eng. 6(2018) 17252-17257.
doi: 10.1021/acssuschemeng.8b04652
L.Y. Xie, L.L. Jiang, J.X. Tan, et al., ACS Sustain. Chem. Eng. 7(2019) 14153-14160.
doi: 10.1021/acssuschemeng.9b02822
S. Paul, J.H. Ha, G.E. Park, Y.R. Lee, Adv. Synth. Catal. 359(2017) 1515-1521.
doi: 10.1002/adsc.201700070
J. Yuan, S. Liu, L. Qu, Adv. Synth. Catal. 359(2017) 4197-4207.
doi: 10.1002/adsc.201701058
L. Wang, P. Bao, W. Liu, et al., Chin. J. Org. Chem. 38(2018) 3189-3196.
doi: 10.6023/cjoc201807014
M. Gao, Y. Li, L. Xie, R. Chauvin, X. Cui, Chem. Commun. 52(2016) 2846-2849.
doi: 10.1039/C5CC08049E
K.J. Li, Y.Y. Jiang, K. Xu, C.C. Zeng, B.G. Sun, Green Chem. 21(2019) 4412-4421.
doi: 10.1039/C9GC01474H
J. Wang, B. Sun, L. Zhang, et al., Org. Chem. Front. 7(2020) 113-118.
doi: 10.1039/C9QO01055F
L. Yang, P. Gao, X.H. Duan, Y.R. Gu, L.N. Guo, Org. Lett. 20(2018) 1034-1037.
doi: 10.1021/acs.orglett.7b03984
L.Y. Xie, Y.L. Chen, L. Qin, et al., Org. Chem. Front. 6(2019) 3950-3955.
doi: 10.1039/C9QO01240K
J. Zhou, P. Zhou, T. Zhao, Q. Ren, J. Li, Adv. Synth. Catal. 361(2019) 5371-5382.
doi: 10.1002/adsc.201901008
J. Xu, H. Yang, H. Cai, et al., Org. Lett. 21(2019) 4698-4702.
doi: 10.1021/acs.orglett.9b01578
L.Y. Xie, Y.S. Liu, H.R. Ding, et al., Chin. J. Catal. 41(2020) 1168-1173.
doi: 10.1016/S1872-2067(19)63526-6
Q.W. Gui, F. Teng, S.N. Ying, et al., Chin. Chem. Lett. 31(2020) 3241-3244.
doi: 10.1016/j.cclet.2020.07.017
L.H. Lu, Z. Wang, W. Xia, et al., Chin. Chem. Lett. 30(2019) 1237-1240.
doi: 10.1016/j.cclet.2019.04.033
Q. Huang, L. Zhu, D. Yi, X. Zhao, W. Wei, Chin. Chem. Lett. 31(2019) 373-376.
Z. Gan, G. Li, Q. Yan, et al., Green Chem. 22(2020) 2956-2962.
doi: 10.1039/D0GC00070A
D. Hu, L. Yang, J.P. Wan, Green Chem. 22(2020) 6773-6777.
doi: 10.1039/D0GC02806A
L. Yang, J.P. Wan, Green Chem. 22(2020) 3074-3078.
doi: 10.1039/D0GC00738B
Q.W. Gui, X. He, W. Wang, et al., Green Chem. 22(2020) 118-122.
doi: 10.1039/C9GC02657F
Y. Wu, J.Y. Chen, J. Ning, et al., Green Chem. 23(2021) 3950-3954.
doi: 10.1039/D1GC00562F
J. Shen, J. Xu, L. Huang, Q. Zhu, P. Zhang, Adv. Synth. Catal. 362(2020) 230-241.
doi: 10.1002/adsc.201901314
C.D. Clinton, C.D. Prasad, R.S. Thombal, Y.R. Lee, Adv. Synth. Catal. 363(2021) 776-784.
doi: 10.1002/adsc.202001182
Z. Shao, S. Zhang, Y. Chen, et al., Tetrahedron 76(2020) 131199.
doi: 10.1016/j.tet.2020.131199
N. Meng, L. Wang, Q. Liu, et al., J. Org. Chem. 85(2020) 6888-6896.
doi: 10.1021/acs.joc.9b03505
H.S. Dutta, A. Ahmad, A.A. Khan, et al., Adv. Synth. Catal. 361(2019) 5534-5539.
doi: 10.1002/adsc.201901212
J.R. Chen, X.Q. Hu, L.Q. Lu, W.J. Xiao, Chem. Soc. Rev. 45(2016) 2044-2056.
doi: 10.1039/C5CS00655D
Z.J. Shen, H.N. Shi, W.J. Hao, S.J. Tu, B. Jiang, Chem. Commun. 54(2018) 11542-11545.
doi: 10.1039/C8CC06086J
Y. Chen, L.Q. Lu, D.G. Yu, C.J. Zhu, W.J. Xiao, Sci. China Chem. 63(2020) 1652-1658.
doi: 10.1007/s11426-020-9811-6
P. Bao, F. Liu, Y. Lv, et al., Org. Chem. Front. 7(2020) 492-498.
doi: 10.1039/C9QO01334B
W.B. He, L.Q. Gao, X.J. Chen, et al., Chin. Chem. Lett. 31(2020) 1895-1898.
doi: 10.1016/j.cclet.2020.02.011
S. He, X. Chen, F. Zeng, et al., Chin. Chem. Lett. 31(2020) 1863-1867.
doi: 10.1016/j.cclet.2019.12.031
Z. Gan, G. Li, X. Yang, et al., Sci. China. Chem. 63(2020) 1652-1658.
doi: 10.1007/s11426-020-9811-6
L.Y. Xie, T.G. Fang, J.X. Tan, et al., Green Chem. 21(2019) 3858-3863.
doi: 10.1039/C9GC01175G
D.Q. Dong, L.X. Li, G.H. Li, et al., Chin. J. Catal. 40(2019) 1494-1498.
doi: 10.1016/S1872-2067(19)63420-0
Q. Liu, L. Wang, H. Yue, et al., Green Chem. 21(2019) 1609-1613.
doi: 10.1039/C9GC00222G
M.H. Huang, C.F. Zhu, C.L. He, et al., Org. Chem. Front. 5(2018) 1643-1650.
doi: 10.1039/C8QO00098K
Q.Q. Ge, J.S. Qian, J. Xuan, J. Org. Chem. 84(2019) 8691-8701.
doi: 10.1021/acs.joc.9b00552
D. Chen, Y. Sun, D. Dong, Q. Han, Z. Wang, Chin. J. Org. Chem. 40(2020) 4267-4273.
doi: 10.6023/cjoc202006025
S. Peng, Y. Lin, W. He, Chin. J. Org. Chem. 40(2020) 541-542.
doi: 10.6023/cjoc202000006
X.Y. Yu, J.R. Chen, W.J. Xiao, Chem. Rev. 121(2021) 506-561.
doi: 10.1021/acs.chemrev.0c00030
X. Gong, X. Li, W. Xie, J. Wu, S. Ye, Org. Chem. Front. 6(2019) 1863-1867.
doi: 10.1039/C9QO00410F
S. Garbarino, D. Ravelli, S. Protti, A. Basso, Angew. Chem. Int. Ed. 55(2016) 15476-15484.
doi: 10.1002/anie.201605288
X. Gong, M. Yang, J.B. Liu, et al., Green Chem. 22(2020) 1906-1910.
doi: 10.1039/D0GC00332H
Y. Li, T. Miao, P. Li, L. Wang, Org. Lett. 20(2018) 1735-1739.
doi: 10.1021/acs.orglett.8b00171
Y. Lv, P. Bao, H. Yue, J.S. Li, W. Wei, Green Chem. 21(2019) 6051-6055.
doi: 10.1039/C9GC03253C
D. Zheng, A. Studer, Org. Lett. 21(2019) 325-329.
doi: 10.1021/acs.orglett.8b03849
N. Meng, Y. Lv, Q. Liu, et al., Chin. Chem. Lett. 32(2021) 258-262.
doi: 10.1016/j.cclet.2020.11.034
M.D. McReynolds, J.M. Dougherty, P.R. Hanson, Chem. Rev. 104(2004) 2239-2258.
doi: 10.1021/cr020109k
Q.A. Acton, Sulfones-Advances in Research and Application, Scholarly Editions, Atlanta, 2013.
Q. Yu, Y. Liu, J.P. Wan, Chin. Chem. Lett. 32(2021) 3514-3517.
doi: 10.1016/j.cclet.2021.04.037
L. Wang, M. Zhang, Y. Zhang, et al., Chin. Chem. Lett. 31(2020) 67-70.
doi: 10.1016/j.cclet.2019.05.041
W. Wei, C. Liu, D. Yang, et al., Chem. Commun. 49(2013) 10239-10241.
doi: 10.1039/c3cc45803b
Q. Liu, F. Liu, H. Yue, et al., Adv. Synth. Catal. 361(2019) 5277-5282.
doi: 10.1002/adsc.201900984
Q. Liu, Y. Lv, R. Liu, et al., Chin. Chem. Lett. 32(2021) 136-139.
doi: 10.1016/j.cclet.2020.11.059
T.Y. Shang, L.H. Lu, Z. Cao, et al., Chem. Commun. 55(2019) 5408-5419.
doi: 10.1039/C9CC01047E
S. He, X. Chen, F. Zeng, et al., Chin. Chem. Lett. 31(2020) 1863-1867.
doi: 10.1016/j.cclet.2019.12.031
A.K. Ghosh, S. Mondal, A. Hajra, Org. Lett. 22(2020) 2771-2775.
doi: 10.1021/acs.orglett.0c00759
Q. Lu, J. Zhang, F. Wei, et al., Angew. Chem. Int. Ed. 52(2013) 7156-7159.
doi: 10.1002/anie.201301634
W. Wei, J. Wen, D. Yang, et al., Org. Biomol. Chem. 12(2014) 7678-7681.
doi: 10.1039/C4OB01369G
Z. Peng, Y.Y. Hong, S. Peng, et al., Org. Biomol. Chem. 19(2021) 4537-4541.
doi: 10.1039/D1OB00552A
Yi Luo , Lin Dong . Multicomponent remote C(sp2)-H bond addition by Ru catalysis: An efficient access to the alkylarylation of 2H-imidazoles. Chinese Chemical Letters, 2024, 35(10): 109648-. doi: 10.1016/j.cclet.2024.109648
Xiao-Ming Chen , Lianhui Song , Jun Pan , Fei Zeng , Yi Xie , Wei Wei , Dong Yi . Visible-light-induced four-component difunctionalization of alkenes to construct phosphorodithioate-containing quinoxalin-2(1H)-ones. Chinese Chemical Letters, 2024, 35(11): 110112-. doi: 10.1016/j.cclet.2024.110112
Chunyan Yang , Qiuyu Rong , Fengyin Shi , Menghan Cao , Guie Li , Yanjun Xin , Wen Zhang , Guangshan Zhang . Rationally designed S-scheme heterojunction of BiOCl/g-C3N4 for photodegradation of sulfamerazine: Mechanism insights, degradation pathways and DFT calculation. Chinese Chemical Letters, 2024, 35(12): 109767-. doi: 10.1016/j.cclet.2024.109767
Guoju Guo , Xufeng Li , Jie Ma , Yongjia Shi , Jian Lv , Daoshan Yang . Photocatalyst/metal-free sequential C–N/C–S bond formation: Synthesis of S-arylisothioureas via photoinduced EDA complex activation. Chinese Chemical Letters, 2024, 35(11): 110024-. doi: 10.1016/j.cclet.2024.110024
Wen-Tao Ouyang , Jun Jiang , Yan-Fang Jiang , Ting Li , Yuan-Yuan Liu , Hong-Tao Ji , Li-Juan Ou , Wei-Min He . Sono-photocatalytic amination of quinoxalin-2(1H)-ones with aliphatic amines. Chinese Chemical Letters, 2024, 35(10): 110038-. doi: 10.1016/j.cclet.2024.110038
Tian-Yu Gao , Xiao-Yan Mo , Shu-Rong Zhang , Yuan-Xu Jiang , Shu-Ping Luo , Jian-Heng Ye , Da-Gang Yu . Visible-light photoredox-catalyzed carboxylation of aryl epoxides with CO2. Chinese Chemical Letters, 2024, 35(7): 109364-. doi: 10.1016/j.cclet.2023.109364
Ping Lu , Baoyin Du , Ke Liu , Ze Luo , Abiduweili Sikandaier , Lipeng Diao , Jin Sun , Luhua Jiang , Yukun Zhu . Heterostructured In2O3/In2S3 hollow fibers enable efficient visible-light driven photocatalytic hydrogen production and 5-hydroxymethylfurfural oxidation. Chinese Journal of Structural Chemistry, 2024, 43(8): 100361-100361. doi: 10.1016/j.cjsc.2024.100361
Jing Wang , Zenghui Li , Xiaoyang Liu , Bochao Su , Honghong Gong , Chao Feng , Guoping Li , Gang He , Bin Rao . Fine-tuning redox ability of arylene-bridged bis(benzimidazolium) for electrochromism and visible-light photocatalysis. Chinese Chemical Letters, 2024, 35(9): 109473-. doi: 10.1016/j.cclet.2023.109473
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