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Green synthesis of 2-trifluoromethylquinoline skeletons via organocatalytic N-[(α-trifluoromethyl)vinyl]isatins CN bond activation

文献类型：期刊论文

作者Ji, Cong-Bin7; Xie, Ding-Xiong6; Chen, Mei6; Lan, Ye-Ying6; Zhang, Bao-Hua6; Yang, Ji-Ying2; Kang, Zheng-Hui1; Chen, Shu-Jie6; Zhang, Yu-Wei5,6; Liu, Yun-Lin3,4,6
刊名CHINESE CHEMICAL LETTERS
出版日期2025-07-01
卷号36期号:7页码:10
关键词N-[(alpha-Trifluoromethyl)vinyl]isatins Pfitzinger-type reaction C-N bond cleavage 2-CF3-quinoline-4-carboxamide 2-CF3-quinoline-4-carboxylicester
ISSN号1001-8417
DOI10.1016/j.cclet.2024.110598
通讯作者Yang, Ji-Ying() ; Kang, Zheng-Hui(kangzhenghui@simm.ac.cn) ; Zhang, Yu-Wei(ywzhang@scnu.edu.cn) ; Liu, Yun-Lin(ylliu@gzhu.edu.cn)
英文摘要The Pfitzinger reaction has long served as a notable synthesis pathway for quinoline-4-carboxylic acids. Although recognized for its synthetic potential since its discovery >138 years ago, a truly catalytic variant has remained elusive until now. Herein, we present a novel 2-tert-butyl-1,1,3,3-tetramethylguanidine (BTMG)-catalyzed Pfitzinger reaction that employs N-[(alpha-trifluoromethyl)vinyl]isatins with amines and alcohols, providing direct routes to 2-CF3-quinoline-4-carboxamides and carboxylic esters. This method is not only green and environmentally benign but also accommodates the introduction of other functional groups like CF2H and CO2Me at the C2 position of quinoline skeleton. The utility of this methodology was demonstrated by the broad substrate scope, the late-stage modification of commercial drugs, and the diverse derivatization of quinoline framework. More importantly, this work not only opens up a new avenue for the activation of amide CN bonds in catalytic reaction development, but also unlocks the huge potential of some 2-trifluoromethyl quinolines with strong inhibitory activity against PTP1B or optoelectronic application in organic light-emitting diodes. (c) 2025 Published by Elsevier B.V. on behalf of Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences.
WOS关键词TRIFLUOROACETIMIDOYL CHLORIDES ; AMIDE BOND ; FLUORINE ; ARYL ; TRIFLUOROMETHYLATION ; CYCLIZATION ; QUINOLINES ; ALKYNES
资助项目National Natural Science Foundation of China[22171056] ; National Natural Science Foundation of China[22122402] ; National Natural Science Foundation of China[21801050] ; Outstanding Youth Project of Guangdong Natural Science Foundation[2024B1515020036] ; Outstanding Youth Project of Guangdong Natural Science Foundation[2021B1515020048] ; Guangdong Natural Science Foundation[2023A1515011313] ; Guangdong Natural Science Foundation[2021A1515010510] ; Guangdong Natural Science Foundation[2024A1515030037] ; Tertiary Education Scientific Research Project of Guangzhou Municipal Education Bureau[202235305] ; Open Fund from Key Laboratory of Organofluorine Chemistry ; Shanghai Engineering Re-search Center of Molecular Therapeutics and New Drug Development
WOS研究方向Chemistry
语种英语
WOS记录号WOS:001487733800002
出版者ELSEVIER SCIENCE INC
源URL[http://119.78.100.183/handle/2S10ELR8/317911]  
专题中国科学院上海药物研究所
通讯作者Yang, Ji-Ying; Kang, Zheng-Hui; Zhang, Yu-Wei; Liu, Yun-Lin
作者单位1.Chinese Acad Sci, Zhongshan Inst Drug Discovery, Shanghai Inst Mat Med, Zhongshan 528400, Peoples R China
2.Sun Yat Sen Univ, Sch Pharmaceut Sci, Guangzhou 510006, Peoples R China
3.East China Normal Univ, Shanghai Engn Res Ctr Mol Therapeut & New Drug Dev, Sch Chem & Mol Engn, Shanghai 200241, Peoples R China
4.Chinese Acad Sci, Key Lab Organofluorine Chem, Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China
5.South China Normal Univ, GDMPA Key Lab Proc Control & Qual Evaluat Chiral P, Guangzhou Key Lab Analyt Chem Biomed, Sch Chem, Guangzhou 510006, Peoples R China
6.Guangzhou Univ, Sch Chem & Chem Engn, Guangzhou 510006, Peoples R China
7.Shangrao Normal Univ, Sch Chem & Environm Sci, Shangrao 334001, Peoples R China
推荐引用方式
GB/T 7714		 Ji, Cong-Bin,Xie, Ding-Xiong,Chen, Mei,et al. Green synthesis of 2-trifluoromethylquinoline skeletons via organocatalytic N-[(α-trifluoromethyl)vinyl]isatins CN bond activation[J]. CHINESE CHEMICAL LETTERS,2025,36(7):10.
APA Ji, Cong-Bin.,Xie, Ding-Xiong.,Chen, Mei.,Lan, Ye-Ying.,Zhang, Bao-Hua.,...&Liu, Yun-Lin.(2025).Green synthesis of 2-trifluoromethylquinoline skeletons via organocatalytic N-[(α-trifluoromethyl)vinyl]isatins CN bond activation.CHINESE CHEMICAL LETTERS,36(7),10.
MLA Ji, Cong-Bin,et al."Green synthesis of 2-trifluoromethylquinoline skeletons via organocatalytic N-[(α-trifluoromethyl)vinyl]isatins CN bond activation".CHINESE CHEMICAL LETTERS 36.7(2025):10.

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来源：上海药物研究所

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