Chinese Journal of Organic Chemistry >
Ammonium Persulfate Promotes Trifluoromethylation of Quinoxalin-2(1H)-ones
Received date: 2020-12-28
Revised date: 2021-04-18
Online published: 2021-06-02
Supported by
Important Science & Technology Specific Projects in Hunan Province(2014FJ1010); Natural Science Fundation of Hunan Province(2018JJ2019)
A green and efficient method for the synthesis of 3-trifluoromethylquinoxalin-2(1H)-ones via direct trifluoromethylation of quinoxalin-2(1H)-ones with CF3SO2Na promoted by ammonium persulfate ((NH4)2S2O8) under mild conditions has been developed. This process is scalable and tolerates a wide spectrum of quinoxalin-2(1H)-one derivatives to deliver corresponding products in good to excellent yields. Comparing to the previous methods, this strategy has the advantages of wide functional groups tolerance, high yield and simple operation, providing an efficient synthetic approach to 3-trifluoromethyl- quinoxalin-2(1H)-ones.
Rongnan Yi , Dongxian Liu , Jiangnan He , Mingming Zhao , Xinhua Xu . Ammonium Persulfate Promotes Trifluoromethylation of Quinoxalin-2(1H)-ones[J]. Chinese Journal of Organic Chemistry, 2021 , 41(8) : 3285 -3291 . DOI: 10.6023/cjoc202012046
[1] | Carta, A.; Piras, S.; Loriga, G. Mini-Rev. Med. Chem. 2006, 6, 1179. |
[2] | Shi, L.; Hu, W.; Wu, J.; Zhou, H.; Li, X. Mini-Rev. Med. Chem. 2018, 18, 392. |
[3] | Xu, Z.; Shaw, A. Y.; Dietrich, J.; Cappelli, A. P.; Nichol, G.; Hulme, C. Mol. Diversity 2012, 16, 73. |
[4] | Moustafa, O. J. Chin. Chem. Soc. 2000, 47, 351. |
[5] | Yang, Y.; Zhang, S.; Wu, B.; Ma, M.; Chen, X.; Qin, X.; He, M.; Hussain, S.; Jing, C.; Ma, B.; Zhu, C. Chem. Med. Chem. 2012, 7, 823. |
[6] | Mao, P.; Zhu, J. L.; Yuan, J. W.; Yang, L. R.; Xiao, Y. M.; Zhang, C. S. Chin. J. Org. Chem. 2019, 39, 1529. (in Chinese) |
[6] | (毛璞, 朱军亮, 袁金伟, 杨亮茹, 肖咏梅, 张长森, 有机化学, 2019, 39, 1529.) |
[7] | Wang, L. L.; Bao, P. L.; Liu, W. W.; Liu, S. T.; Hu, C. S.; Yue, H. L.; Yang, D. S.; Wei, W. Chin. J. Org. Chem. 2018, 38, 3189. (in Chinese) |
[7] | (王雷雷, 鲍鹏丽, 刘维维, 刘思彤, 胡昌松, 岳会兰, 杨道山, 魏伟, 有机化学, 2018, 38, 3189.) |
[8] | Hai, M.; Guo, L. N.; Wang, L.; Duan, X. H. Acta Chim. Sinica 2019, 77, 895. (in Chinese) |
[8] | (海曼, 郭丽娜, 王乐, 段新华, 化学学报, 2019, 77, 859.) |
[9] | 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. |
[10] | Yang, L.; Gao, P.; Duan, X. H. Gu, Y. R.; Guo, L. N. Org. Lett. 2018, 20, 1034. |
[11] | Yuan, J. W.; Fu, J. H.; Liu, S. N.; Xiao, Y. N.; Mao, P.; Qu, L. B. Org. Biomol. Chem. 2018, 16, 3203. |
[12] | 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. |
[13] | Gao, M.; Li, Y.; Xie, L.; Chauvin, R.; Cui, X. Chem. Commun. 2016, 52, 2846. |
[14] | Gupta, A.; Deshmukh, M. S.; Jain, N. J. Org. Chem. 2017, 82, 4784. |
[15] | Purser, S.; Moore, P. R.; Swallow, S.; Veronique, G. Chem. Soc. Rev. 2008, 37, 320. |
[16] | Müller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881. |
[17] | Lawrence, D. S.; Copper, J. E.; Smith, C. D. J. Med. Chem. 2001, 44, 594. |
[18] | O'Brien, A. G.; Maruyama, A.; Inokuma, Y.; Fujita, M.; Baran, P. S.; Blackmond, D. G. Angew. Chem., Int. Ed. 2017, 53, 11868. |
[19] | Wang, L.; Zhang, Y.; Li, F. Adv. Synth. Catal. 2018, 360, 3969. |
[20] | Xue, W.; Su, Y.; Wang, K. H.; Cao, L.; Feng, Y.; Zhang, W.; Huang, D.; Hu, Y. Asian J. Org. Chem. 2019, 8, 887. |
[21] | Zheng, Y.; You, Y.; Shen, Q.; Zhang, J.; Liu, L.; Duan, X.-H. Org. Chem. Front. 2020, 7, 2069. |
[22] | Chen, J.-Y.; Li, Y. H.; Mei, L.; Wu, H. Y. Chin. J. Org. Chem. 2019, 39, 3040. (in Chinese) |
[22] | (陈锦杨, 李玉涵, 梅兰, 吴红谕, 有机化学, 2019, 39, 3040.) |
[23] | Liu, K. J.; Deng, J. H.; Yang, J.; Gong, S. F.; Lin, Y. W.; He, J. Y.; Cao, Z.; He, W. M. Green Chem. 2020, 22, 433. |
[24] | Shi, S.-H.; Liang, Y.; Jiao, N. Chem. Rev. 2021, 121, 485. |
[25] | Tang, S.; Liu, Y.; Lei, A. Chem 2018, 4, 27. |
[26] | Kingston, C.; Palkowitz, M. D.; Takahira, Y.; Vantourout, J. C.; Peters, B. K.; Kawamata, Y.; Baran, P. S. Acc. Chem. Res. 2020, 53, 72. |
[27] | Chen, J. Y.; Zhong, C. T.; Gui, Q. W.; Zhou, Y. M.; Fang, Y. Y.; Liu, K. J.; Lin, Y. W.; Cao, Z.; He, W. M. Chin. Chem. Lett. 2021, 32, 475. |
[28] | Chen, J. Y.; Wu, H. Y.; Gui, Q. W.; Yan, S. S.; Deng, J.; Lin, Y. W.; Cao, Z.; He, W. M. Chin. J. Catal. 2021, 42, 1445. |
[29] | Wei, Z. J.; Qi, S. J.; Xu, Y. H.; Liu, H.; Wu, J. Z.; Li, H. S.; Xia, C. C.; Duan, G. Y. Adv. Synth. Catal. 2019, 361, 5490. |
[30] | Wang, J. Y.; Sun, B.; Zhang, L.; Xu, T. W.; Xie, Y. Y.; Jin, C. Asian J. Org. Chem. 2019, 8, 1942. |
[31] | Sutherland, D. R.; Veguillas, M.; Oates, C. L.; Lee, A. L. Org. Lett. 2018, 20, 6863. |
[32] | Jacobsen, E. J.; Tenbrink, R. E.; Stelzer, L. S.; Belonga, K. L.; Im, H. K.; Im, W. B.; Sethy, V. H.; Tang, A. H. J. Med. Chem. 1996, 39, 158. |
[33] | Aoki, K.; Obata, T.; Yamazaki, Y. Chem. Pharm. Bull. 2007, 55, 255. |
[34] | Chen, D.; Wang, Z. J.; Bao, W. J. Org. Chem. 2010, 75, 5768. |
[35] | Carrër, A.; Brion, J. D.; Messaoudi, S.; Alami, M. Org. Lett. 2013, 15, 5606. |
[36] | Landge, S. M.; Torok, B. Catal. Lett. 2008, 22, 338. |
[37] | Dou, G. Y.; Jiang, Y. Y.; Xu, K.; Zeng, C. C. Org. Chem. Front. 2019, 6, 2392. |
/
〈 |
|
〉 |