2142-03-2Relevant articles and documents
Synthesis of imides via palladium-catalyzed three-component coupling of aryl halides, isocyanides and carboxylic acids
Wang, Bo,He, Dan,Ren, Beige,Yao, Tuanli
, p. 900 - 903 (2020)
A palladium-catalyzed three-component synthesis of acyclic imides from feedstock aryl halides, carboxylic acids and isocyanides through the intermediacy of isoimides has been developed. The key to the success of this approach was controlled isocyanide slow addition and organic/aqueous biphasic conditions. This transition-metal-catalyzed approach features readily available starting materials, atom- and step-economy, good functional group compatibility and gram-scale synthetic capability. Utilization of this new method is illustrated in the late-stage functionalization of drugs Carprofen, Loxoprofen and Flurbiprofen. This strategy has also been successfully applied in the synthesis of cyclic imides including phthalimide, homophthalimide, and 2H-2-benzazepine-1,3-dione derivatives.
A rapid synthesis of N-aryl phthalimides under microwave irradiation in the absence of solvent
Li, Hui-Zhang,Zhang, Jin-Song,Zhou, Ya-Ming,Li, Tong-Shuang
, p. 927 - 930 (2002)
A mixture of phthalic anhydride (1) and aromatic amines (2a-h) were irradiated in a microwave oven for 2-10 min to provide N-aryl phthalimides (3a-h) in 91-95% yields.
A New Simple and Efficient Synthesis of N-Aryl Phthalimides in Ionic Liquid [bmim][PF6]
Zhou, Mei-Yun,Li, Yi-Qun,Xu, Xin-Ming
, p. 3777 - 3780 (2003)
The room temperature ionic liquid [bmim][PF6], namely 1-butyl-3-methyl-imidazolium hexafluorophosphate, is used as an alternative solvent to classic solvents for the synthesis of a series of N-aryl phthalimides in good to excellent yields.
“On water” nano-Cu2O-catalyzed CO-free one-pot multicomponent cascade cyanation-annulation-aminolysis reaction toward phthalimides
Wen, Xiaowei,Liu, Xiaojuan,Yang, Zhiqi,Xie, Menglan,Liu, Yuxi,Long, Lipeng,Chen, Zhengwang
supporting information, p. 1738 - 1743 (2021/03/14)
An efficient nano-Cu2O-catalyzed cascade multicomponent reaction of 2-halobenzoic acids and trimethylsilyl cyanide with diverse amines was developed using water as a solvent, affording versatileN-substituted phthalimide derivatives in moderate to excellent yields. This novel strategy features carbon monoxide gas-free, environmentally benign, one-pot multistep transformation, commercially available reagents, a cheap catalyst without any additives, wide functional group tolerance, and operational convenience.
Palladium Catalyzed Regioselective Synthesis of Substituted Biaryl Amides through Decarbonylative Arylation of Phthalimides
Samanta, Partha Kumar,Biswas, Papu
, p. 3968 - 3976 (2019/03/26)
The Pd(OAc)2 catalyzed cross-coupling of N-substituted phthalimides with aryl halide provides a single step direct access of a wide range of synthetically appealing ortho-substituted biarylamides in high yields through unique carbonyl (CO) replacement. The reaction proceeds through a ligand-free condition and is well tolerant to the diverse functionality of both imide and halide units. The reaction negates any requirement of organometallic reagent and needs a shorter reaction time and comparatively lower temperature as required for previously reported decarbonylative processes.
