Synthesis and Biological Activities of New 4-PhenylanilinesContaining the Diphenyl Ether Moiety

doi:10.6023/cjoc201904049

Chinese Journal of Organic Chemistry ›› 2019, Vol. 39 ›› Issue (10): 2851-2859.DOI: 10.6023/cjoc201904049 Previous Articles Next Articles

ARTICLE

含二苯醚结构的联苯胺类衍生物的合成及活性研究

汪万强^a, 程兰^a, 彭宏英^a, 姚维忠^a, 张锐^a, 陈宬^b^*(), 程华^a^*()

^a 湖北文理学院化学化工与食品科学学院襄阳 441053
^b 武汉理工大学材料复合新技术国家重点实验室武汉 430070

收稿日期:2019-04-19 修回日期:2019-05-23 发布日期:2019-06-06
通讯作者: 陈宬,程华 E-mail:chengchen@whut.edu.cn;cch510@126.com
基金资助:
国家自然科学基金(21502062);湖北文理学院教师科研能力培育基金(2018kypy001);湖北文理学院学科开放基金资助项目(XK2019039)

Synthesis and Biological Activities of New 4-PhenylanilinesContaining the Diphenyl Ether Moiety

Wang Wanqiang^a, Cheng Lan^a, Peng Hongying^a, Yao Weizhong^a, Zhang Rui^a, Chen Cheng^b^*(), Cheng Hua^a^*()

^a Department of Chemical Engineering and Food Science, Hubei University of Arts and Science, Xiangyang 441053
^b State Key Laboratory of Advanced Technology for Materials Synthesis and Processing,Wuhan University of Technology, Wuhan 430070

Received:2019-04-19 Revised:2019-05-23 Published:2019-06-06
Contact: Chen Cheng,Cheng Hua E-mail:chengchen@whut.edu.cn;cch510@126.com
Supported by:
Project supported by the National Natural Science Foundation of China(21502062);The Teachers' Scientific Research Ability Cultivation Fund of Hubei University of Arts and Science(2018kypy001);The Open Foundation of Discipline of Hubei University of Arts and Science(XK2019039)

According to the principle of "splicing-up" bioactive substructures, a new series of target compounds were designed and synthesized by incorporating a diphenyl ether moiety into 4-phenylanilines. Moreover, the structures of the synthesized compounds were confirmed by ¹H NMR, ¹³C NMR, HRMS and melting points measurements. The inhibitory activities of these compounds were evaluated against succinate-cytochrome reductase (SCR). Based on the bioassay results, target compound N-(4-(2-chloro-4-(trifluoromethyl)phenoxy)-3-fluorophenyl)-[1,1'-biphenyl]-4-amine (3o) exhibited an inhibition rate of 46.44% at a concentration of 10 μmol?L ^–1, which demonstrated potential values for further investigations.

Key words: 4-phenylanilines, diphenyl ether, synthesis, biological activities

Cite this article

Wang Wanqiang, Cheng Lan, Peng Hongying, Yao Weizhong, Zhang Rui, Chen Cheng, Cheng Hua. Synthesis and Biological Activities of New 4-PhenylanilinesContaining the Diphenyl Ether Moiety[J]. Chinese Journal of Organic Chemistry, 2019, 39(10): 2851-2859.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 5

References 47

[1]	Cheng, H.; Song, W.; Nie, R.; Wang, Y. X.; Li, H. L.; Jiang, X. S.; Wu, J. J.; Cheng, C.; Wu, Q.Y. Bioorg. Med. Chem. Lett. 2018, 28, 1330. doi: 10.1016/j.bmcl.2018.03.014
[2]	Li, L. K.; Yuan, S. K.; Pan, H. Y.; Wang, Y. Agrochemicals 2011, 50, 165 (in Chinese).
	( 李良孔, 袁善奎, 潘洪玉, 王岩, 农药, 2011, 50, 165.)
[3]	Ye, Y. H.; Ma, L.; Dai, Z. C.; Xiao, Y.; Zhang, Y. Y.; Li, D. D.; Wang, J. X.; Zhu, H.L. J. Agric. Food Chem. 2014, 62, 4063.
[4]	Zhu, X. L.; Xiong, L.; Li, H.; Song, X. Y.; Liu, J. J.; Yang, G. F . ChemMedChem . 2014, 9, 1512. doi: 10.1002/cmdc.201300456
[5]	Cheng, H.; Shen, Y. Q.; Pan, X. Y.; Hou, Y. P.; Wu, Q. Y.; Yang, G.F. New J. Chem. 2015, 39, 7281.
[6]	Xiong, L.; Zhu, X. L.; Shen, Y. Q.; Wishwa, W. K. W. M.; Li, K.; Yang, G.F. Eur. J. Med. Chem. 2015, 95, 424.
[7]	Xiong, L.; Zhu, X. L.; Gao, H. W.; Fu, Y.; Hu, S. Q.; Jiang, L. N.; Yang, W. C.; Yang, G.F. J. Agric. Food Chem. 2016, 64, 4830.
[8]	Yao, T. T.; Xiao, D. X.; Li, Z. S.; Cheng, J. L.; Fang, S. W.; Du, Y. J.; Zhao, J. H.; Dong, X. W.; Zhu, G.N. J. Agric. Food Chem. 2017, 65, 5397.
[9]	Xiong, L.; Li, H.; Jiang, L. N.; Ge, J. M.; Yang, W. C.; Zhu, X. L.; Yang, G.F. J. Agric. Food Chem. 2017, 65, 1021.
[10]	Jin, H.; Zhou, J. Y.; Pu, T.; Zhang, A. G.; Gao, X. H.; Tao, K.; Hou, T.P. Bioorg. Chem. 2017, 73, 76.
[11]	Zhang, A. G.; Zhou, J. Y.; Tao, K.; Hou, T. P.; Jin, H. Bioorg. Med. Chem. Lett. 2018, 28, 3042. doi: 10.1016/j.bmcl.2018.08.001
[12]	He, L. M.; Cui, K. D.; Song, Y. F.; Mu, W.; Liu, F. J. Agric. Food Chem. 2018, 66, 6692.
[13]	Du, S. J.; Qin, Z.H. Chin. J. Pestic. Sci. 2018, 20, 545 (in Chinese).
	( 杜士杰, 覃兆海 , 农药学学报, 2018, 20, 545.)
[14]	Yan, W.; Wang, X.; Li, K.; Li, T. X.; Wang, J. J.; Yao, K. C.; Cao, L. L.; Zhao, S. S.; Ye, Y.H. Pestic. Biochem. Physiol. 2019, 156, 160.
[15]	Slater, E.C.; Biochim. Biophys. ActaRev. Bioenerg. 1973, 301, 129.
[16]	Clough, J. M.; Godfrey, C. R. A.; Godwin, J. R.; Joseph, R. S. I.; Spinks, C. . Pestic. Outlook, 1996, 7, 16.
[17]	Ypema, H. L.; Gold, R.E. Plant Dis. 1999, 83, 4. doi: 10.1094/PDIS.1999.83.1.4
[18]	Ueki, M.; Machida, K.; Taniguchi, M . Curr. Opin. Anti-Infect. Invest. Drugs. 2000, 2, 387. doi: 10.1016/0960-9822(92)90088-R
[19]	Mitani, S.; Araki, S.; Takii, Y.; Ohshima, T.; Matsuo, N.; Miyoshi, H. Pestic. Biochem. Physiol. 2001, 71, 107.
[20]	Ohshima, T.; Komyoji, T.; Mitani, S.; Matsuo, N.; Nakajima, T. J. Pestic. Sci. 2004, 29, 147.
[21]	Bolgunas, S.; Clark, D. A.; Hanna, W. S.; Mauvais, P. A.; Pember, S.O. J. Med. Chem. 2006, 49, 4762.
[22]	Kruglov, A. G.; Andersson, M. A.; Mikkola, R.; Roivainen, M.; Kredics, L.; Saris, N. E. L.; Salkinoja-Salonen, M.S. Chem. Res. Toxicol. 2009, 22, 565.
[23]	Berry, E. A.; Huang, L. S.; Lee, D. W.; Daldal, F.; Nagai, K.; Minagawa, N. Biochim. Biophys. Acta, Bioenerg. 2010, 1797, 360.
[24]	Zhao, P. L.; Wang, L.; Zhu, X. L.; Huang, X.; Zhan, C. G.; Wu, J. W.; Yang, G.F. J. Am. Chem. Soc. 2010, 132, 185.
[25]	Wang, F.; Li, H.; Wang, L.; Yang, W. C.; Wu, J. W.; Yang, G.F., Bioorg. Med. Chem. 2011, 19, 4608.
[26]	Vallières, C.; Fisher, N.; Antoine, T.; Al-Helal, M.; Stocks, P.; Berry, N. G.; Lawrenson, A. S.; Ward, S. A.; O'Neill, P. M.; Biagini, G. A.; Meunier, B. Antimicrob. Agents Chemother. 2012, 56, 3739.
[27]	Hao, G. F.; Wang, F.; Li, H.; Zhu, X. L.; Yang, W. C.; Huang, L. S.; Wu, J. W.; Berry, E. A.; Yang, G.F. J. Am. Chem. Soc. 2012, 134, 11168.
[28]	Yang, W. C.; Li, H.; Wang, F.; Zhu, X. L.; Yang, G. F . ChemBioChem. 2012, 13, 1542. doi: 10.1002/cbic.201200295
[29]	Zhu, X. L.; Wang, F.; Li, H.; Yang, W. C.; Chen, Q.; Yang, G. F . Chin. J. Chem. 2012, 30, 1999.
[30]	Capper, M. J.; O'Neill, P. M.; Fisher, N.; Strange, R. W.; Moss, D.; Ward, S. A.; Berry, N. G.; Lawrenson, A. S.; Hasnain, S. S.; Biagini, G. A.; Antonyuk, S.V. Proc. Natl. Acad. Sci. 2015, 112, 755.
[31]	Zhu, X. L.; Zhang, M. M.; Liu, J. J.; Ge, J. M.; Yang, G.F. J. Agric. Food Chem. 2015, 63, 3377.
[32]	Fehr, M.; Wolf, A.; Stammler, G. Pest Manage. Sci. 2016, 72, 591.
[33]	Chen, C.; Wu, Q. Y.; Shan, L. Y.; Zhang, B.; Verpoort, F.; Yang, G.F. RSC Adv. 2016, 6, 97580. doi: 10.1039/C6RA19424A
[34]	Cheng, H.; Wang, W. Q.; Huang, L.; Cui, P.; Wu, Q.Y. Chin. J. Org. Chem. 2016, 36, 1065 (in Chinese).
	( 程华, 汪万强, 黄琳, 崔萍, 吴琼友, 有机化学, 2016, 36, 1065.)
[35]	Cheng, H.; Nie, R.; Wang, W. Q.; Huang, L.; Liu, K.; Chen, C.; Wu, Q.Y. Chin. J. Org. Chem. 2017, 37, 1368 (in Chinese).
	( 程华, 聂忍, 汪万强, 黄琳, 刘科, 陈宬, 吴琼友, 有机化学, 2017, 37, 1368.)
[36]	Alday, P. H.; Bruzual, I.; Nilsen, A.; Pou, S.; Winter, R.; Mamoun, C. B.; Riscoe, M. K.; Doggett, J.S. Antimicrob. Agents Chemother. 2017, 61, e01866-16.
[37]	Song, Z.; Iorga, B. I.; Mounkoro, P.; Fisher, N.; Meunier, B. FEBS Lett. 2018, 592, 1346. doi: 10.1002/feb2.2018.592.issue-8
[38]	Cheng, H.; Fu, Y.; Chang, Q.; Zhang, N.; Bu, M. W.; Niu, Y.; Wu, Q. Y.; Chen, C; Verpoort, F. . Chin. Chem. Lett. 2018, 29, 1897.
[39]	Zhu, X. L.; Zhang, R.; Wu, Q. Y.; Song, Y. J.; Wang, Y. X.; Yang, J. F.; Yang, G.F. J. Agric. Food Chem. 2019, 67, 2774.
[40]	KingS, T. E. Method.Enzymol. 1967, 10, 216.
[41]	Yu, C. A.; Yu, L.; King, T.E. J. Biol. Chem. 1974, 249, 4905.
[42]	Yu, C. A; Yu, L. . Biochim. Biophys. Acta, Bioenerg. 1980, 591, 409.
[43]	, Zhang, Y.PB. 2002, Worldestic. 24, 6 (in Chinese).
	( 张一宾, 世界农药, 2002, 24, 6.)
[44]	Sternberg, J. A.; Geffken, D.; Adams Jr, J. B.; Pōstages, R.; Sternberg, C. G.; Campbell, C. L.; Moberg, W.K. Pest Manage. Sci., 2001, 57, 143.
[45]	Strathmann, S.; Walker, S.; Barnes, J. Phytopathology, 2011, 101, S172
[46]	Avenot, H. F.; Michailides, T. J. Crop Prot. 2010, 29, 643.
[47]	Wu, S. Y.; Lan, L. A.; Jiang, J. J.; Ding, X. T.; Ho, C. M.; Lou, Y. F.; Fan, G.R. Pharm. Biomed. Anal. 2019, 168, 44. doi: 10.1016/j.jpba.2019.02.006

Entry	[Cu] (equiv.)	Base (equiv.)	Solvent	Time/ h	Yield^a/ %
1	Cu(OAc)₂ (1.00)	K₂CO₃ (2.00)	DMF	60	65
2	Cu(OAc)₂?H₂O (1.00)	K₂CO₃ (2.00)	DMF	60	58
3	CuCl₂ (1.00)	K₂CO₃ (2.00)	DMF	60	Trace
4	CuCl₂?2H₂O (1.00)	K₂CO₃ (2.00)	DMF	60	Trace
5	CuBr₂ (1.00)	K₂CO₃ (2.00)	DMF	60	Trace
6	CuCl (1.00)	K₂CO₃ (2.00)	DMF	60	Trace
7	CuBr (1.00)	K₂CO₃ (2.00)	DMF	60	Trace
8	CuI (1.00)	K₂CO₃ (2.00)	DMF	60	Trace
9	Cu(OAc)₂ (1.00)	Cs₂CO₃ (2.00)	DMF	60	Trace
10	Cu(OAc)₂ (1.00)	Pyridine (2.00)	DMF	60	Trace
11	Cu(OAc)₂ (1.00)	Et₃N (2.00)	DMF	48	75
12	Cu(OAc)₂ (1.00)	Et₃N (2.00)	DCM	48	84
13	Cu(OAc)₂ (1.00)	Et₃N (2.00)	MeCN	48	90
14	Cu(OAc)₂ (0.50)	Et₃N (2.00)	MeCN	72	70
15	Cu(OAc)₂ (0.25)	Et₃N (2.00)	MeCN	72	65
16	Cu(OAc)₂ (1.00)	Et₃N (2.00)	MeCN	72	30

Entry	[Cu] (equiv.)	Base (equiv.)	Solvent	Time/ h	Yield^a/ %
1	Cu(OAc)₂ (1.00)	K₂CO₃ (2.00)	DMF	60	65
2	Cu(OAc)₂?H₂O (1.00)	K₂CO₃ (2.00)	DMF	60	58
3	CuCl₂ (1.00)	K₂CO₃ (2.00)	DMF	60	Trace
4	CuCl₂?2H₂O (1.00)	K₂CO₃ (2.00)	DMF	60	Trace
5	CuBr₂ (1.00)	K₂CO₃ (2.00)	DMF	60	Trace
6	CuCl (1.00)	K₂CO₃ (2.00)	DMF	60	Trace
7	CuBr (1.00)	K₂CO₃ (2.00)	DMF	60	Trace
8	CuI (1.00)	K₂CO₃ (2.00)	DMF	60	Trace
9	Cu(OAc)₂ (1.00)	Cs₂CO₃ (2.00)	DMF	60	Trace
10	Cu(OAc)₂ (1.00)	Pyridine (2.00)	DMF	60	Trace
11	Cu(OAc)₂ (1.00)	Et₃N (2.00)	DMF	48	75
12	Cu(OAc)₂ (1.00)	Et₃N (2.00)	DCM	48	84
13	Cu(OAc)₂ (1.00)	Et₃N (2.00)	MeCN	48	90
14	Cu(OAc)₂ (0.50)	Et₃N (2.00)	MeCN	72	70
15	Cu(OAc)₂ (0.25)	Et₃N (2.00)	MeCN	72	65
16	Cu(OAc)₂ (1.00)	Et₃N (2.00)	MeCN	72	30

Entry	Compd.	R¹	R²	Yield^a/%	I^b/%
1	3a	H	H	90	30.42
2	3b	4-Br	H	76	36.95
3	3c	2,4-Cl₂	H	71	36.09
4	3d	2-Cl-4-CF₃	H	86	39.01
5	3e	2-Br-4-Cl	H	74	32.16
6	3f	2,4,6-Cl₃	2-Cl	94	13.72
7	3g	2,4-Cl₂	2-Cl	69	6.30
8	3h	2-Me-4-Cl	2-Cl	67	12.71
9	3i	2-Cl-4-CF₃	2-Cl	74	24.47
10	3j	2-Br-4-Cl	2-Cl	68	6.81
11	3k	2-Naphthyl^c	2-Cl	76	5.73
12	3l	1-Br-2-naphthyl^c	2-Cl	70	1.91
13	3m	2,4-Cl₂	2-F	75	37.70
14	3n	2-Me-4-Cl	2-F	95	37.39
15	3o	2-Cl-4-CF₃	2-F	73	46.44
16	3p	2,4,6-Cl₃	2-F	70	16.02
17	3q	2-Naphthyl^c	2-F	65	20.59
18	3r	1-Br-2-naphthyl^c	2-F	76	7.62
19	3s	2,4-Cl₂	2,6-Cl₂	50	4.07
20	3t	2-Br-4-Cl	2,6-Cl₂	54	10.07
21	3u	2-Naphthyl^c	2,6-Cl₂	78	26.09
22	3v	1-Br-2-naphthyl^c	2,6-Cl₂	71	3.74
23	3w	2,4-Cl₂	2,6-F₂	81	38.96
24	3x	4-Cl-2-Me	2,6-F₂	68	37.78
25	3y	2-Br-4-Cl	2,6-F₂	62	43.25
26	3z	2-Naphthyl^c	2,6-F₂	61	43.20
27	3a'	1-Br-2-naphthyl^c	2,6-F₂	68	10.23
28	嘧菌酯^d				95.95

Entry	Compd.	R¹	R²	Yield^a/%	I^b/%
1	3a	H	H	90	30.42
2	3b	4-Br	H	76	36.95
3	3c	2,4-Cl₂	H	71	36.09
4	3d	2-Cl-4-CF₃	H	86	39.01
5	3e	2-Br-4-Cl	H	74	32.16
6	3f	2,4,6-Cl₃	2-Cl	94	13.72
7	3g	2,4-Cl₂	2-Cl	69	6.30
8	3h	2-Me-4-Cl	2-Cl	67	12.71
9	3i	2-Cl-4-CF₃	2-Cl	74	24.47
10	3j	2-Br-4-Cl	2-Cl	68	6.81
11	3k	2-Naphthyl^c	2-Cl	76	5.73
12	3l	1-Br-2-naphthyl^c	2-Cl	70	1.91
13	3m	2,4-Cl₂	2-F	75	37.70
14	3n	2-Me-4-Cl	2-F	95	37.39
15	3o	2-Cl-4-CF₃	2-F	73	46.44
16	3p	2,4,6-Cl₃	2-F	70	16.02
17	3q	2-Naphthyl^c	2-F	65	20.59
18	3r	1-Br-2-naphthyl^c	2-F	76	7.62
19	3s	2,4-Cl₂	2,6-Cl₂	50	4.07
20	3t	2-Br-4-Cl	2,6-Cl₂	54	10.07
21	3u	2-Naphthyl^c	2,6-Cl₂	78	26.09
22	3v	1-Br-2-naphthyl^c	2,6-Cl₂	71	3.74
23	3w	2,4-Cl₂	2,6-F₂	81	38.96
24	3x	4-Cl-2-Me	2,6-F₂	68	37.78
25	3y	2-Br-4-Cl	2,6-F₂	62	43.25
26	3z	2-Naphthyl^c	2,6-F₂	61	43.20
27	3a'	1-Br-2-naphthyl^c	2,6-F₂	68	10.23
28	嘧菌酯^d				95.95

含二苯醚结构的联苯胺类衍生物的合成及活性研究

Synthesis and Biological Activities of New 4-PhenylanilinesContaining the Diphenyl Ether Moiety

RichHTML

PDF

Knowledge

Abstract

Cite this article

share this article

Fig. & Tab. 5

References 47

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Penghui Li, Qingyang Xie, Fuxian Wan, Yuanhong Zhang, Lin Jiang. Synthesis and Fungicidal Activity of Novel Substituted Pyrimidine-5-carboxamides Bearing Cyclopropyl Moiety [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 650-656.
[2]	Fakai Zou, Nengzhong Wang, Hui Yao, Hui Wang, Mingguo Liu, Nianyu Huang. Regio- and Stereo-selective Synthesis of 1β-/3R-Aryl Thiosugar [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 593-604.
[3]	Luyao Li, Zhongwen He, Zhenguo Zhang, Zhenhua Jia, Teck-Peng Loh. Application of Triaryl Carbenium in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 421-437.
[4]	Qinggang Mei, Qinghan Li. Recent Progress of Visible Light-Induced the Synthesis of C(3) (Hetero)arylthio Indole Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 398-408.
[5]	Weiqing Yang, Yanbing Ge, Yuanyuan Chen, Ping Liu, Haiyan Fu, Menglin Ma. Design and Synthesis of Fluorescent 1,8-Napthalimide Derivatives and Their Identification of Cysteine [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 180-194.
[6]	Qianfan Zhao, Yongzheng Chen, Shiming Zhang. Application and Mechanism Study of Carbon-Based Metal-Free Catalysts in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 137-147.
[7]	Shan Chen, Zhilin Chen, Qiong Hu, Yanshuang Meng, Yue Huang, Pingfang Tao, Liru Lu, Guobao Huang. Recognition of Bis-thiourea Tweezers to Neutral Molecules in Non-Polar Solvent [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 277-281.
[8]	Huakun Wang, Xiaolong Ren, Yining Xuan. Study of the Halide Salt Catalyzed [3＋2] Cycloaddition of α,β-Epoxy Carboxylate with Isocyanate [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 251-258.
[9]	Yukun Jin, Baoyi Ren, Fushun Liang. Visible Light-Mediated Selective C—F Bond Cleavage of Trifluoromethyl Groups and Its Application in Synthesizing gem-Difluoro-Containing Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 85-110.
[10]	Cuiyun Ma, Hailan Luo, Fuhua Zhang, Dan Guo, Shuxing Chen, Fei Wang. Green Biosynthesis, Photophysical Properties and Application of 3-Pyrrolyl BODIPY [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 216-223.
[11]	Bozhen Wang, Jie Zhang, Chunhui Nian, Mingming Jin, Miaomiao Kong, Wulan Li, Wenfei He, Jianzhang Wu. Synthesis and Antitumor Activity of 3,4-Dichlorophenyl Amides [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 232-241.
[12]	Shihang Yu, Jiawei Liu, Biyu An, Qinghua Bian, Min Wang, Jiangchun Zhong. Asymmetric Synthesis of the Contact Sex Pheromone of Neoclytus acuminatus acuminatus (Fabricius) [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 301-308.
[13]	Yang Li, Jinding Yuan, Di Zhao. Deep Eutectic Solvent of 1,3-Dimethylurea/L-(+)-Tartaric Acid for the Green Synthesis of (E)-2-Styrylquinoline-3-carboxylic Acid Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3268-3276.
[14]	Dandan Sui, Nannan Cen, Ruoqu Gong, Yang Chen, Wenbo Chen. Supporting-Electrolyte-Free Electrochemical Synthesis of Trifluoromethylated Oxindoles in Continuous Flow [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3239-3245.
[15]	Ruixia Cao, Yuping Jia. Synthesis and Biological Activity of Novel Pyrrolo[2,3-d]pyrimidine Derivatives Containing Coumarin [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3304-3311.