Ammonium Persulfate Promotes Trifluoromethylation of Quinoxalin-2(1H)-ones

doi:10.6023/cjoc202012046

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (8): 3285-3291.DOI: 10.6023/cjoc202012046 Previous Articles Next Articles

NOTES

过硫酸铵促进喹喔啉-2(1H)-酮三氟甲基化反应

易荣楠^a^,^b, 刘冬娴^a, 贺江南^a, 赵明明^a, 许新华^b^,^*()

a 湖南警察学院刑事科学技术系长沙 410138
b 湖南大学化学化工学院化学传感与计量学国家重点实验室长沙 410082

收稿日期:2020-12-28 修回日期:2021-04-18 发布日期:2021-06-02
通讯作者: 许新华
基金资助:
湖南省科技重大专项(2014FJ1010); 湖南省自然科学基金(2018JJ2019)

Ammonium Persulfate Promotes Trifluoromethylation of Quinoxalin-2(1H)-ones

Rongnan Yi^a^,^b, Dongxian Liu^a, Jiangnan He^a, Mingming Zhao^a, Xinhua Xu^b()

a Department of Criminal Technology, Hunan Police Academy, Changsha 410138
b State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082

Received:2020-12-28 Revised:2021-04-18 Published:2021-06-02
Contact: Xinhua Xu
Supported by:
Important Science & Technology Specific Projects in Hunan Province(2014FJ1010); Natural Science Fundation of Hunan Province(2018JJ2019)

1. .pdf(3507KB)

Abstract

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.

Key words: ammonium persulfate, trifluoromethylation, quinoxalin-2(1H)-one derivatives, CF₃SO₂Na

Cite this article

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.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 5

References 37

[1]	Carta, A.; Piras, S.; Loriga, G. Mini-Rev. Med. Chem. 2006, 6, 1179. pmid: 17100630
[2]	Shi, L.; Hu, W.; Wu, J.; Zhou, H.; Li, X. Mini-Rev. Med. Chem. 2018, 18, 392. doi: 10.2174/1389557517666171101111134
[3]	Xu, Z.; Shaw, A. Y.; Dietrich, J.; Cappelli, A. P.; Nichol, G.; Hulme, C. Mol. Diversity 2012, 16, 73. doi: 10.1007/s11030-011-9354-x
[4]	Moustafa, O. J. Chin. Chem. Soc. 2000, 47, 351. doi: 10.1002/jccs.v47.2
[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. doi: 10.1002/cmdc.v7.5
[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) doi: 10.6023/cjoc201904025
	(毛璞, 朱军亮, 袁金伟, 杨亮茹, 肖咏梅, 张长森, 有机化学, 2019, 39, 1529.) doi: 10.6023/cjoc201904025
[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) doi: 10.6023/cjoc201807014
	(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.) doi: 10.6023/cjoc201807014
[8]	Hai, M.; Guo, L. N.; Wang, L.; Duan, X. H. Acta Chim. Sinica 2019, 77, 895. (in Chinese) doi: 10.6023/A19040155
	(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. doi: 10.1039/D0GC02844D
[10]	Yang, L.; Gao, P.; Duan, X. H. Gu, Y. R.; Guo, L. N. Org. Lett. 2018, 20, 1034. doi: 10.1021/acs.orglett.7b03984 pmid: 29364685
[11]	Yuan, J. W.; Fu, J. H.; Liu, S. N.; Xiao, Y. N.; Mao, P.; Qu, L. B. Org. Biomol. Chem. 2018, 16, 3203. doi: 10.1039/C8OB00206A
[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. doi: 10.1039/C9GC03899J
[13]	Gao, M.; Li, Y.; Xie, L.; Chauvin, R.; Cui, X. Chem. Commun. 2016, 52, 2846. doi: 10.1039/C5CC08049E
[14]	Gupta, A.; Deshmukh, M. S.; Jain, N. J. Org. Chem. 2017, 82, 4784. doi: 10.1021/acs.joc.7b00464
[15]	Purser, S.; Moore, P. R.; Swallow, S.; Veronique, G. Chem. Soc. Rev. 2008, 37, 320. doi: 10.1039/B610213C
[16]	Müller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881. pmid: 17901324
[17]	Lawrence, D. S.; Copper, J. E.; Smith, C. D. J. Med. Chem. 2001, 44, 594. pmid: 11170649
[18]	O'Brien, A. G.; Maruyama, A.; Inokuma, Y.; Fujita, M.; Baran, P. S.; Blackmond, D. G. Angew. Chem., Int. Ed. 2017, 53, 11868. doi: 10.1002/anie.201407948
[19]	Wang, L.; Zhang, Y.; Li, F. Adv. Synth. Catal. 2018, 360, 3969. doi: 10.1002/adsc.v360.20
[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. doi: 10.1002/ajoc.v8.6
[21]	Zheng, Y.; You, Y.; Shen, Q.; Zhang, J.; Liu, L.; Duan, X.-H. Org. Chem. Front. 2020, 7, 2069. doi: 10.1039/D0QO00497A
[22]	Chen, J.-Y.; Li, Y. H.; Mei, L.; Wu, H. Y. Chin. J. Org. Chem. 2019, 39, 3040. (in Chinese) doi: 10.6023/cjoc201904022
	(陈锦杨, 李玉涵, 梅兰, 吴红谕, 有机化学, 2019, 39, 3040.) doi: 10.6023/cjoc201904022
[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. doi: 10.1039/C9GC03713F
[24]	Shi, S.-H.; Liang, Y.; Jiao, N. Chem. Rev. 2021, 121, 485. doi: 10.1021/acs.chemrev.0c00335 pmid: 33017147
[25]	Tang, S.; Liu, Y.; Lei, A. Chem 2018, 4, 27. doi: 10.1016/j.chempr.2017.10.001
[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. doi: 10.1021/acs.accounts.9b00539
[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. doi: 10.1016/j.cclet.2020.09.034
[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. doi: 10.1016/S1872-2067(20)63750-0
[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. doi: 10.1002/adsc.v361.23
[30]	Wang, J. Y.; Sun, B.; Zhang, L.; Xu, T. W.; Xie, Y. Y.; Jin, C. Asian J. Org. Chem. 2019, 8, 1942. doi: 10.1002/ajoc.v8.10
[31]	Sutherland, D. R.; Veguillas, M.; Oates, C. L.; Lee, A. L. Org. Lett. 2018, 20, 6863. doi: 10.1021/acs.orglett.8b02988 pmid: 30354158
[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. pmid: 8568803
[33]	Aoki, K.; Obata, T.; Yamazaki, Y. Chem. Pharm. Bull. 2007, 55, 255. doi: 10.1248/cpb.55.255
[34]	Chen, D.; Wang, Z. J.; Bao, W. J. Org. Chem. 2010, 75, 5768. doi: 10.1021/jo101253a
[35]	Carrër, A.; Brion, J. D.; Messaoudi, S.; Alami, M. Org. Lett. 2013, 15, 5606. doi: 10.1021/ol4028946
[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. doi: 10.1039/C9QO00552H

过硫酸铵促进喹喔啉-2(1H)-酮三氟甲基化反应

Ammonium Persulfate Promotes Trifluoromethylation of Quinoxalin-2(1H)-ones

RichHTML

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

Fig. & Tab. 5

References 37

Related Articles 15

Recommended Articles

Metrics

Comments

Entry	Oxidant (equiv.)	Solvent	Temp./℃	Time/h	Yield^b/%
1	(NH₄)₂S₂O₈ (2.0)	DMSO	80	15	78
2	(NH₄)₂S₂O₈ (2.0)	DMF	80	15	65
3	(NH₄)₂S₂O₈ (2.0)	DCE	80	15	31
4	(NH₄)₂S₂O₈ (2.0)	DMSO	90	15	76
5	(NH₄)₂S₂O₈ (2.0)	DMSO	100	15	72
6	(NH₄)₂S₂O₈ (2.0)	DMSO	70	15	68
7	(NH₄)₂S₂O₈ (2.0)	DMSO	60	15	59
8	(NH₄)₂S₂O₈ (2.0)	DMSO	80	10	65
9	(NH₄)₂S₂O₈ (2.0)	DMSO	80	20	82
10	(NH₄)₂S₂O₈ (2.0)	DMSO	80	25	82
11	K₂S₂O₈ (2.0)	DMSO	80	20	79
12	PhI(OAc)₂ (2.0)	DMSO	80	20	72
13	TBHP (2.0)	DMSO	80	20	52
14	Oxone (2.0)	DMSO	80	20	75
15	None	DMSO	80	20	Trace
16	O₂	DMSO	80	20	35
17	(NH₄)₂S₂O₈ (1.0)	DMSO	80	20	70
18	(NH₄)₂S₂O₈ (3.0)	DMSO	80	20	82

[1]	Rui Wang, Lang Gao, Cen Zhou, Xiao Zhang. Haloperfluoroalkylation of Unactivated Terminal Alkenes over Phenylphenothiazine-Based Porous Organic Polymers [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1136-1145.
[2]	Qingyun Gu, Zhenfeng Cheng, Xiaobao Zeng. Electrochemical Oxidative Trifluoromethylation of α-Oxoketene Ketene Dithioacetals with CF₃SO₂Na [J]. Chinese Journal of Organic Chemistry, 2022, 42(5): 1537-1544.
[3]	Xiaolong Guo, Yuxian Wang, Zhiqiang Zhao, Qing Wang, Jian Zuo, Luyao Wang. Electrochemical Oxidative C—H Trifluoromethylation of Quinoxalin-2(1H)-ones and the Performance Evaluation via Electro-descriptors [J]. Chinese Journal of Organic Chemistry, 2022, 42(2): 641-649.
[4]	Ransong Ma, Zhoubin Deng, Kehu Wang, Danfeng Huang, Yulai Hu, Xiaobo Lü. Research Progress of Trifluoromethylation Involving CF₃Br [J]. Chinese Journal of Organic Chemistry, 2022, 42(2): 353-362.
[5]	Yunliang Qiu, Fengjiao Wei, Liu Ye, Minyue Zhao. Advances in Trifluoromethylation-Promoted Functional Group Migration of Alkenes [J]. Chinese Journal of Organic Chemistry, 2021, 41(5): 1821-1834.
[6]	Jun Pan, Jingjing Wu, Fanhong Wu. Progress in Fluoroalkylation of Multicomponent [J]. Chinese Journal of Organic Chemistry, 2021, 41(3): 983-1001.
[7]	Bing Mu, Junliang Wu, Guang'an Zhang. Alternative Approach for the Synthesis of Nitroaromatic Olefins via Dehydrogenative Nitration of Easily Available Arylethanes [J]. Chinese Journal of Organic Chemistry, 2021, 41(1): 250-257.
[8]	Ouyang Yao, Xu Xiuhua, Qing Fengling. Oxidative Coupling Reactions of Arylboronic Acids and Fluoroform-Derived AgCF₃ [J]. Chinese Journal of Organic Chemistry, 2020, 40(10): 3426-3430.
[9]	Liu Tao, Qu Chuanhua, Xie Jin, Zhu Chengjian. Photoinduced Atom-Economical Iterative Hydrotrifluoromethylation of Terminal Alkynes and Remote C(sp³)-H Functionalization [J]. Chin. J. Org. Chem., 2019, 39(6): 1613-1622.
[10]	Ji Xiaoming, Shi Guangfa, Zhang Yanghui. Progress of Trifluoromethylation Using Trifluoroacetic Acid and Its Derivatives as CF₃-Sources [J]. Chin. J. Org. Chem., 2019, 39(4): 929-939.
[11]	Wang Na, Gu Qiang-Shuai, Cheng Yong-Feng, Li Lei, Li Zhong-Liang, Guo Zhen, Liu Xin-Yuan. Visible-Light Promoted Preparation of Trifluoromethylated Tetrahydrofuran and Tetrahydropyran [J]. Chin. J. Org. Chem., 2019, 39(1): 200-206.
[12]	Wang Qing, Gao Kecheng, Zou Jianping, Zeng Runsheng. Copper(I)-Catalyzed Non-terminal Enamides Trifluoromethylation: Flexible Synthesis of N-(3,3,3-Trifluoro-2-arylprop-1-en-1-yl) Substituted Benzamide [J]. Chin. J. Org. Chem., 2018, 38(4): 863-870.
[13]	Chen Donghan, Yang Wen, Yao Yongqi, Yang Xin, Deng Yingying, Yang Dingqiao. Recent Advances in Transition Metal-Promoted Trifluoromethylation Reactions [J]. Chin. J. Org. Chem., 2018, 38(10): 2571-2589.
[14]	Hui Renjie, Zhang Shiwei, Tan Zheng, Wu Xiaopei, Feng Bainian. Research Progress of Trifluoromethylation with Sodium Trifluoromethanesulfinate [J]. Chin. J. Org. Chem., 2017, 37(12): 3060-3075.
[15]	Kang Juan, Huang Danfeng, Wang Kehu, Su Yingpeng, Hu Yulai, Chang Qing. Synthesis of α-Trifluoromethyl-α-hydroxyl Weinreb Amides [J]. Chin. J. Org. Chem., 2017, 37(1): 103-109.