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Synthesis 2023; 55(03): 443-450
DOI: 10.1055/a-1899-5409
DOI: 10.1055/a-1899-5409
paper
Visible-Light-Induced Recyclable g-C3N4 Catalyzed C–H Hydroxylation of Quinoxalin-2(1H)-ones
We are grateful to the National Natural Science Foundation of China (22101082) and the Natural Science Foundation of Hunan Provincial Natural Science Foundation of China (2020JJ5203).
Abstract
A visible-light-promoted hydroxylation of quinoxalin-2(1H)-ones using recyclable graphitic carbon nitride (g-C3N4) as a heterogeneous photocatalyst has been developed. This protocol enables the selective synthesis of various hydroxyl-containing quinoxalin-2(1H)-ones in good to excellent yields under an ambient air atmosphere. Importantly, this heterogeneous catalyst can be used at least six times without significant loss of activity.
Key words
visible light - quinoxalin-2(1H)-ones - hydroxylation - g-C3N4 - heterogeneous photocatalystsSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1899-5409.
- Supporting Information
Publication History
Received: 18 May 2022
Accepted after revision: 13 July 2022
Accepted Manuscript online:
13 July 2022
Article published online:
20 September 2022
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References
- 1a Ackermann L. Acc. Chem. Res. 2014; 47: 281
- 1b Arockiam PB, Bruneau C, Dixneuf PH. Chem. Rev. 2012; 112: 5879
- 1c Giri R, Shi B.-F, Engle KM, Maugel N, Yu J.-Q. Chem. Soc. Rev. 2009; 38: 3242
- 1d Lyons TW, Sanford MS. Chem. Rev. 2010; 110: 1147
- 2a Göbel D, Clamor N, Lork E, Nachtsheim BJ. Org. Lett. 2019; 21: 5373
- 2b Enthaler S, Company A. Chem. Soc. Rev. 2011; 40: 4912
- 3a Shah SS, Paul A, Bera M, Venkatesh Y, Singh ND. P. Org. Lett. 2018; 20: 5533
- 3b Liu C.-K, Chen M.-Y, Lin X.-X, Fang Z, Guo K. Green Chem. 2020; 22: 6437
- 3c Mondal S, Hajra A. J. Org. Chem. 2018; 83: 11392
- 4a Blöcher R, Rodarte Ramírez A, Castro-Escarpulli G, Curiel-Quesada E, Reyes-Arellano A. Molecules 2018; 23: 3075
- 4b Hussain S, Parveen S, Hao X, Zhang S, Wang W, Qin X, Yang Y, Chen X, Zhu S, Zhu C, Ma B. Eur. J. Med. Chem. 2014; 80: 383
- 4c Carta A, Piras S, Loriga G, Paglietti G. Mini-Rev. Med. Chem. 2006; 6: 1179
- 4d Monge A, Martinez-Crespo FJ, Lopez de Cerain A, Palop JA, Narro S, Senador V, Marin A, Sainz Y, Gonzalez M. J. Med. Chem. 1995; 38: 4488
- 5a He X.-K, Lu J, Zhang A.-J, Zhang Q.-Q, Xu G.-Y, Xuan J. Org. Lett. 2020; 22: 5984
- 5b Niu K, Song L, Hao Y, Liu Y, Wang Q. Chem. Commun. 2020; 56: 11673
- 5c 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
- 5d Yan Z, Sun B, Zhang X, Zhuang X, Yang J, Su W, Jin C. Chem. Asian J. 2019; 14: 3344
- 5e Zhang H, Xu J, Zhou M, Zhao J, Zhang P, Li W. Org. Biomol. Chem. 2019; 17: 10201
- 5f Hong G, Yuan J, Fu J, Pan G, Wang Z, Yang L, Xiao Y, Mao P, Zhang X. Org. Chem. Front. 2019; 6: 1173
- 5g Jin S, Yao H, Lin S, You X, Yang Y, Yan Z. Org. Biomol. Chem. 2020; 18: 205
- 5h Peng S, Liu J.-J, Yang L. Org. Biomol. Chem. 2021; 19: 9705
- 5i Rong X, Jin L, Gu Y, Liang G, Xia Q. Asian J. Org. Chem. 2020; 9: 185
- 5j Wang L, Zhao J, Sun Y, Zhang H.-Y, Zhang Y. Eur. J. Org. Chem. 2019; 6935
- 5k Yang L, Gao P, Duan X.-H, Gu Y.-R, Guo LN. Org. Lett. 2018; 20: 1034
- 5l Yuan J, Fu J, Yin J, Dong Z, Xiao Y, Mao P, Qu L. Org. Chem. Front. 2018; 5: 2820
- 5m Zhou J, Ren Q, Xu N, Wang C, Song S, Chen Z, Li J. Green Chem. 2021; 23: 5753
- 6a Jiang X, Yang L, Ye Z, Du X, Fang L, Zhu Y, Chen K, Li J, Yu C. Eur. J. Org. Chem. 2020; 1687
- 6b Xie L.-Y, Liu Y.-S, Ding H.-R, Gong S.-F, Tan J.-X, He J.-Y, Cao Z, He W.-M. Chin. J. Catal. 2020; 41: 1168
- 6c Yang Q, Han X, Zhao J, Zhang H.-Y, Zhang Y. J. Org. Chem. 2019; 84: 11417
- 6d Zhao L, Wang L, Gao Y, Wang Z, Li P. Adv. Synth. Catal. 2019; 361: 5363
- 6e Zhou J, Zhou P, Zhao T, Ren Q, Li J. Adv. Synth. Catal. 2019; 361: 5371
- 7a Guo J, Zhang L, Du X, Zhang L, Cai Y, Xia Q. Eur. J. Org. Chem. 2021; 2230
- 7b Gupta A, Deshmukh MS, Jain N. J. Org. Chem. 2017; 82: 4784
- 7c Li K.-J, Xu K, Liu Y.-G, Zeng C.-C, Sun B.-G. Adv. Synth. Catal. 2019; 361: 1033
- 7d Li Y, Gao M, Wang L, Cui X. Org. Biomol. Chem. 2016; 14: 8428
- 7e Sun M, Wang L, Zhao L, Wang Z, Li P. ChemCatChem 2020; 12: 5261
- 7f Wei W, Wang L, Bao P, Shao Y, Yue H, Yang D, Yang X, Zhao X, Wang H. Org. Lett. 2018; 20: 7125
- 8a Teng Q.-H, Yao Y, Wei W.-X, Tang H.-T, Li J.-R, Pan Y.-M. Green Chem. 2019; 21: 6241
- 8b 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
- 8c Zhou J, Li Z, Sun Z, Ren Q, Zhang Q, Li H, Li J. J. Org. Chem. 2020; 85: 4365
- 9a Bao P, Liu F, Lv Y, Yue H, Li J.-S, Wei W. Org. Chem. Front. 2020; 7: 492
- 9b Lu J, He X.-K, Cheng X, Zhang A.-J, Xu G.-Y, Xuan J. Adv. Synth. Catal. 2020; 362: 2178
- 9c Ni H, Li Y, Shi X, Pang Y, Jin C, Zhao F. Tetrahedron Lett. 2021; 68: 152915
- 9d Ni H, Shi X, Li Y, Zhang X, Zhao J, Zhao F. Org. Biomol. Chem. 2020; 18: 6558
- 9e Xie L.-Y, Bai Y.-S, Xu X.-Q, Peng X, Tang H.-S, Huang Y, Lin Y.-W, Cao Z, He W.-M. Green Chem. 2020; 22: 1720
- 9f Yuan J.-W, Fu J.-H, Liu S.-N, Xiao Y.-M, Mao P, Qu L.-B. Org. Biomol. Chem. 2018; 16: 3203
- 9g Zeng X, Liu C, Wang X, Zhang J, Wang X, Hu Y. Org. Biomol. Chem. 2017; 15: 8929
- 9h Zhu H.-L, Zeng F.-L, Chen X.-L, Sun K, Li H.-C, Yuan X.-Y, Qu L.-B, Yu B. Org. Lett. 2021; 23: 2976
- 10a Bao H, Lin Z, Jin M, Zhang H, Xu J, Chen B, Li W. Tetrahedron Lett. 2021; 66: 152841
- 10b Carrër A, Brion J.-D, Messaoudi S, Alami M. Org. Lett. 2013; 15: 5606
- 10c Dutta NB, Bhuyan M, Baishya G. RSC Adv. 2020; 10: 3615
- 10d Liu X, Liu Z, Xue Y, Li J, Zou D, Wu Y, Wu Y. Tetrahedron Lett. 2020; 61: 152612
- 10e Paul S, Ha JH, Park GE, Lee YR. Adv. Synth. Catal. 2017; 359: 1515
- 10f Paul S, Khanal HD, Clinton CD, Kim SH, Lee YR. Org. Chem. Front. 2019; 6: 231
- 10g Leilei W, Pengli B, Weiwei L, Sitong L, Changsong H, Huilan Y, Daoshan Y, Wei W. Chin. J. Org. Chem. 2018; 38: 3189
- 10h Xu J, Zhang H, Zhao J, Ni Z, Zhang P, Shi B.-F, Li W. Org. Chem. Front. 2020; 7: 4031
- 10i Yin K, Zhang R. Org. Lett. 2017; 19: 1530
- 10j Yuan J, Liu S, Qu L. Adv. Synth. Catal. 2017; 359: 4197
- 11a Gao M, Li Y, Xie L, Chauvin R, Cui X. Chem. Commun. 2016; 52: 2846
- 11b Hu C, Hong G, Zhou C, Tang Z.-C, Han J.-W, Wang L.-M. Asian J. Org. Chem. 2019; 8: 2092
- 11c Kim Y, Kim DY. Tetrahedron Lett. 2018; 59: 2443
- 11d Mai W.-P, Yuan J.-W, Zhu J.-L, Li Q.-Q, Yang L.-R, Xiao Y.-M, Mao P, Qu L.-B. ChemistrySelect 2019; 4: 11066
- 11e Rawat D, Kumar R, Subbarayappa A. Green Chem. 2020; 22: 6170
- 12a Xue W, Su Y, Wang K.-H, Cao L, Feng Y, Zhang W, Huang D, Hu Y. Asian J. Org. Chem. 2019; 8: 887
- 12b Dou G.-Y, Jiang Y.-Y, Xu K, Zeng C.-C. Org. Chem. Front. 2019; 6: 2392
- 12c Wang J, Sun B, Zhang L, Xu T, Xie Y, Jin C. Asian J. Org. Chem. 2019; 8: 1942
- 12d Wang L, Zhang Y, Li F, Hao X, Zhang H.-Y, Zhao J. Adv. Synth. Catal. 2018; 360: 3969
- 12e Wei Z, Qi S, Xu Y, Liu H, Wu J, Li H, Xia C, Duan G. Adv. Synth. Catal. 2019; 361: 5490
- 13 Peng S, Hu D, Hu J.-L, Lin Y.-W, Tang S.-S, Tang H.-S, He J.-Y, Cao Z, He W.-M. Adv. Synth. Catal. 2019; 361: 5721
- 14 Sau S, Mal P. Eur. J. Org. Chem. 2022; e202200425
- 15a Liu J, Wang H, Antonietti M. Chem. Soc. Rev. 2016; 45: 2308
- 15b Ong W.-J, Tan L.-L, Ng YH, Yong S.-T, Chai S.-P. Chem. Rev. 2016; 116: 7159
- 15c Wang X, Maeda K, Thomas A, Takanabe K, Xin G, Carlsson JM, Domen K, Antonietti M. Nat. Mater. 2009; 8: 76
- 16a Savateev A, Ghosh I, König B, Antonietti M. Angew. Chem. Int. Ed. 2018; 57: 15936
- 16b Lakhi KS, Park D.-H, Al-Bahily K, Cha W, Viswanathan B, Choy J.-H, Vinu A. Chem. Soc. Rev. 2017; 46: 72
- 17a Geng P, Tang Y, Pan G, Wang W, Hu J, Cai Y. Green Chem. 2019; 21: 6116
- 17b Su F, Mathew SC, Möhlmann L, Antonietti M, Wang X, Blechert S. Angew. Chem. Int. Ed. 2011; 50: 657
- 17c Wang H, Jia R, Hong M, Miao H, Ni B, Niu T. Green Chem. 2021; 23: 6591
- 18a Cavedon C, Madani A, Seeberger PH, Pieber B. Org. Lett. 2019; 21: 5331
- 18b Ghosh I, Khamrai J, Savateev A, Shlapakov N, Antonietti M, König B. Science 2019; 365: 360
- 18c He Y, Dan X, Tang Y, Yang Q, Wang W, Cai Y. Green Chem. 2021;
- 18d Ni B, Zhang B, Han J, Peng B, Shan Y, Niu T. Org. Lett. 2020; 22: 670
- 18e Shi T, Sun K, Chen X.-L, Zhang Z.-X, Huang X.-Q, Peng Y.-Y, Qu L.-B, Yu B. Adv. Synth. Catal. 2020; 362: 2143
- 18f Wang J, Xue L, Hong M, Ni B, Niu T. Green Chem. 2020; 22: 411
- 19a Fu X.-Y, Si Y.-F, Qiao L.-P, Zhao Y.-F, Chen X.-L, Yu B. Adv. Synth. Catal. 2022; 364: 574
- 19b Si Y.-F, Chen X.-L, Fu X.-Y, Sun K, Song X, Qu L.-B, Yu B. ACS Sustainable Chem. Eng. 2020; 8: 10740
- 19c Zeng F.-L, Zhu H.-L, Chen X.-L, Qu L.-B, Yu B. Green Chem. 2021; 23: 3677
- 20a 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
- 20b Xie L.-Y, Peng S, Yang L.-H, Peng C, Lin Y.-W, Yu X, Cao Z, Peng Y.-Y, He W.-M. Green Chem. 2021; 23: 374
- 21 Tyson EL, Niemeyer ZL, Yoon TP. J. Org. Chem. 2014; 79: 1427
- 22 Wu W.-B, Wong Y.-C, Tan Z.-K, Wu J. Catal. Sci. Technol. 2018; 8: 4257
- 23 Xie D, Wang Y, Xie J, Lu J, Cui J, Zhang M, Fu L, Wang Y. Med. Chem. Res. 2014; 23: 4977
- 24 Akula PS, Hong B.-C, Lee G.-H. RSC Adv. 2018; 8: 19580
- 25 Miyake Y, Itoh Y, Hatanaka A, Suzuma Y, Suzuki M, Kodama H, Arai Y, Suzuki T. Bioorg. Med. Chem. 2019; 27: 1119
- 26 Loev B, Musser JH, Brown RE, Jones H, Kahen R, Huang FC, Khandwala A, Sonnino-Goldman P, Leibowitz MJ. J. Med. Chem. 1985; 28: 363