Visible-Light-Induced Methylation of Quinoxalin-2(1H)-ones Catalyzed by Dye Molecules

Abstract

A visible-light-driven, molecular dye-catalyzed C-3 methylation strategy for quinoxalin-2(1H)-ones has been successfully developed. The methodology demonstrates broad substrate compatibility with various substituted quinoxalin-2(1H)-ones, which could react with N,N,N′,N′,N′′-pentamethyldiethylenetriamine (PMDETA) efficiently at room temperature under ambient atmospheric conditions to afford the corresponding 3-methylquinoxalinone derivatives in moderate to good yields. It is noteworthy that this protocol offers a simple, clean, and transition-metal-free approach, establishing a practical and eco-friendly methodology for constructing diverse C3-methylated quinoxalinone scaffolds, complementing existing synthetic strategies for site-selective functionalization of these heterocycles.

Key words

photocatalysis - methylation - quinoxalin-2(1H)-ones - dye molecules - photosensitizers

Publikationsverlauf

Eingereicht: 18. April 2025

Angenommen nach Revision: 20. Mai 2025

Artikel online veröffentlicht:
12. Juni 2025

• References

• 1a Li X, Yang K, Li W, Xu W. Drugs Future 2006; 31: 979
• 1b Akins PT, Atkinson RP. Curr. Med. Res. Opin. 2002; 18: 9
• 2a Carta A, Piras S, Loriga G, Paglietti G. Mini-Rev. Med. Chem. 2006; 6: 1179
• 2b Liang Q, Zhang Y, Huang M, Xiao Y, Xiao F. Mol. Med. Rep. 2019; 19: 1256
• 2c Xie W, Wu Y, Zhang J, Mei Q, Zhang Y, Zhu N, Liu R, Zhang H. Eur. J. Med. Chem. 2018; 145: 35
• 3a Xie W, Xie S, Zhou Y, Tang X, Liu J, Yang W, Qiu M. Eur. J. Med. Chem. 2014; 81: 22
• 3b Abbas H.-AS, Al-Marhabi AR, Eissa SI, Ammar YA. Bioorg. Med. Chem. 2015; 23: 6560
• 4 Qin X, Hao X, Han H, Zhu S, Yang Y, Wu B, Hussain S, Parveen S, Jing C, Ma B, Zhu C. J. Med. Chem. 2015; 58: 1254
• 5 Nishio T. J. Chem. Soc., Perkin Trans. 1 1990; 565
• 6 Kalinin AA, Mamedov VA. Russ. J. Org. Chem. 2009; 45: 1098
• 7 Yuan J, Fu J, Yin J, Dong Z, Xiao Y, Mao P, Qu L. Org. Chem. Front. 2018; 5: 2820
• 8a Yang L, Gao P, Duan X.-H, Gu Y.-R, Guo LN. Org. Lett. 2018; 20: 1034
• 8b Zheng K, Chen C, Wang Y, Xu H, Ge K, Shen C. Org. Lett. 2025; 27: 4747
• 8c Dong J, Xuan L, Wang C, Zhao C, Wang H, Yan Q, Wang W, Chen F. Chin. J. Org. Chem. 2024; 44: 111
• 8d Hong Y, Xu J, Chen A, Du Y, Wang G, Shen J, Zhang P. Org. Lett. 2025; 27: 2526
• 9 Peng S, Liu JJ, Yang L. Org. Biomol. Chem. 2021; 19: 9705
• 10 Liu X, Guo Z, Liu Y, Chen X, Li J, Zou D, Wu Y, Wu Y. Org. Biomol. Chem. 2022; 20: 1391
• 11 Liu F, Ye Z.-P, Hu Y.-Z, Gao J, Zheng L, Chen K, Xang H.-Y, Chen X.-Q, Yang H. J. Org. Chem. 2021; 86: 11905
• 12 Zhang L, He J, Zhang P, Zheng K, Shen C. Mol. Catal. 2022; 519: 112145
• 13a Xu J, Zhang Y, Xu R, Wang Y, Shen J, Li W. Org. Chem. Front. 2024; 11: 5122
• 13b Zheng K, Wang Z, Wang Y, Chen C, Shen C. Adv. Synth. Catal. 2025; 367: e202500018
• 13c Li Y, Xu J, Wang Y, Xu R, Zhao Y, Li W. J. Org. Chem. 2025; 90: 1683
• 14 Xie L.-Y, Jiang L.-L, Tan J.-X, Wang Y, Xu X.-Q, Zhang B, Zhong C, He WM. ACS Sustainable Chem. Eng. 2019; 7: 14153
• 15a Mane KD, Kamble RB, Suryavanshi G. New J. Chem. 2019; 43: 7403
• 15b Kang W.-J, Li B, Duan M, Pan G, Sun W, Ding A, Zhang Y, Houk KN, Guo H. Angew. Chem. Int. Ed. 2022; 61: e202211562
• 15c Kang W.-J, Li B, Zhao Z, Sun S, Feng C, Hu K, Houk KN, Guo H. ACS Catal. 2023; 13: 13588
• 15d Li J, Xu J, Chen B, Pang Q, Shen J, Wang K, Zhang P. J. Org. Chem. 2025; 90: 1354
• 16a Xia P.-J, Hu Y.-Z, Ye Z.-P, Li X.-J, Xiang H.-Y, Yang H. J. Org. Chem. 2020; 85: 3538
• 16b Sau S, Takizawa S, Kim HY, Oh K. Org. Lett. 2024; 26: 8821
• 16c Carrer A, Brion JD, Messaoudi S, Alami M. Org. Lett. 2013; 15: 5606
• 16d Pal B, Mal P. Org. Lett. 2025; 27: 978
• 16e Chen D, Bao W. Adv. Synth. Catal. 2010; 352: 955
• 16f Sau S, Mal P. Eur. J. Org. Chem. 2022; e202200425
• 16g Liu S, Huang Y, Qing F.-L, Xu X.-H. Org. Lett. 2018; 20: 5497
• 16h Ghosh P, Kwon NY, Kim S, Han S, Lee SH, An W, Mishra NK, Han SB, Kim IS. Angew. Chem. Int. Ed. 2021; 60: 191
• 16i Su H.-Y, Zhu X.-L, Huang Y, Xu X.-H, Qing F.-L. Chem. Commun. 2020; 56: 12805
• 16j Gao R, Wang F, Geng X, Li C.-Y, Wang L. Org. Lett. 2022; 24: 7118
• 17 Wang L, Zhao J, Sun Y, Zhang H.-Y, Zhang Y. Eur. J. Org. Chem. 2019; 6935
• 18 Zhu Y, Zhang Y, Zhao X, Lu K. Org. Biomol. Chem. 2024; 22: 8951
• 19 Wang J, Wang Y, Lin W, Yang A, Wang Y, Wang J, Zhen H, Ge H. J. Org. Chem. 2024; 89: 17482
• 20 Ramkumar N, Plantus K, Ozola M, Mishnev A, Nikolajeva V, Senkovs M, Ošeka M, Veliks J. New J. Chem. 2023; 47: 20642
• 21 Xue W, Su Y, Wang K.-H, Zhang R, Feng Y, Cao L, Huang D, Hu Y. Org. Biomol. Chem. 2019; 17: 6654
• 22 Zhang T.-B, Guan X.-D, Gao Y, Lu S.-C, Li B.-L. Org. Biomol. Chem. 2024; 22: 3439