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 ha...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-[(α-trifluoromethyl)vinyl]isatins with amines and alcohols,providing direct routes to 2-CF_(3)-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 CF_(2)H and CO_(2)Me 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 C-N 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.展开更多
目前广泛应用的含Cr的薄膜有Cr N薄膜,以及以Cr N薄膜为基础,通过添加Si和C元素形成的Cr Si N薄膜、Cr CN薄膜和Cr Si CN薄膜。综述上述4种薄膜的结构及其力学和摩擦学特性的研究进展,阐述在不同摩擦环境下掺杂元素含量对薄膜摩擦因数...目前广泛应用的含Cr的薄膜有Cr N薄膜,以及以Cr N薄膜为基础,通过添加Si和C元素形成的Cr Si N薄膜、Cr CN薄膜和Cr Si CN薄膜。综述上述4种薄膜的结构及其力学和摩擦学特性的研究进展,阐述在不同摩擦环境下掺杂元素含量对薄膜摩擦因数和磨损率的影响,指出Si和C元素的掺杂均能改善Cr N薄膜的摩擦学性能,并从结构角度分析其原因。展开更多
基金National Natural Science Foundation of China(Nos.22171056,22122402,21801050)Outstanding Youth Project of Guangdong Natural Science Foundation(Nos.2024B1515020036,2021B1515020048)+3 种基金Guangdong Natural Science Foundation(Nos.2023A1515011313,2021A1515010510,2024A1515030037)Tertiary Education Scientific Research Project of Guangzhou Municipal Education Bureau(No.202235305)the Open Fund from Key Laboratory of Organofluorine ChemistryShanghai Engineering Research Center of Molecular Therapeutics and New Drug Development are gratefully acknowledged for financial support.
文摘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-[(α-trifluoromethyl)vinyl]isatins with amines and alcohols,providing direct routes to 2-CF_(3)-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 CF_(2)H and CO_(2)Me 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 C-N 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.
文摘目前广泛应用的含Cr的薄膜有Cr N薄膜,以及以Cr N薄膜为基础,通过添加Si和C元素形成的Cr Si N薄膜、Cr CN薄膜和Cr Si CN薄膜。综述上述4种薄膜的结构及其力学和摩擦学特性的研究进展,阐述在不同摩擦环境下掺杂元素含量对薄膜摩擦因数和磨损率的影响,指出Si和C元素的掺杂均能改善Cr N薄膜的摩擦学性能,并从结构角度分析其原因。
