Subscribe to RSS
DOI: 10.1055/s-0043-1775495
Visible-Light-Induced Methylation of Quinoxalin-2(1H)-ones Catalyzed by Dye Molecules
We sincerely thank the Natural Science Foundation of Liaoning Province (LJ212410149027), Liaoning Revitalization Talents Program (XLYC1902085), and China Petrochemical Corporation Innovation Project (223020) for financial support.
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.
Supporting Information
- Supporting information for this article is available online at https://doi-org.accesdistant.sorbonne-universite.fr/10.1055/s-0043-1775495.
- Supporting Information
Publication History
Received: 18 April 2025
Accepted after revision: 20 May 2025
Article published online:
12 June 2025
© 2025. Thieme. All rights reserved
Georg Thieme Verlag KG
Oswald-Hesse-Straße 50, 70469 Stuttgart, Germany
-
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