13533-66-9Relevant academic research and scientific papers
Iron-Catalyzed Synthesis of Oxindoles: Application to the Preparation of Pyrroloindolines
Correia, Valquírio G.,Abreu, Juliana C.,Barata, Caio A. E.,Andrade, Leandro H.
, p. 1060 - 1063 (2017)
A novel and highly efficient synthetic approach to pyrroloindolines has been developed. The process is based on tandem radical addition/cyclization with inexpensive iron catalyst. This method tolerates a wide range of N-methyl-N-arylacrylamides as well carbamoyl radicals, providing access to a variety of functionalized 3,3-disubstituted oxindoles, key intermediates for many bioactive pyrroloindolines such as (±)-esermethole, (±)-deoxyeseroline, and (±)-physovenol methyl ether.
Synthesis of Perfluoroalkyl-Substituted Oxindoles through Organophotoredox-Catalyzed Perfluoroalkylation of N-arylacrylamides with Perfluoroalkyl Iodides
Yang, Zhiyong,Tang, Anjiang
supporting information, p. 1061 - 1066 (2019/05/24)
An efficient process was developed for the perfluoroalkylation of N -arylacrylamides through an organocatalyzed photoredox/cyclization reaction of N -arylacrylamides with inexpensive perfluoroalkyl iodide reagents. The reaction employs an inexpensive organic dye, eosin Y, as the photoredox catalyst and is run under irradiation by a 26 W LED lightbulb.
Catalyst-free and selective trifluoromethylative cyclization of acryloanilides using PhICF3Cl
Guo, Jia,Xu, Cong,Wang, Ling,Huang, Wanqiao,Wang, Mang
supporting information, p. 4593 - 4599 (2019/05/17)
Trifluoromethylation-triggered cyclization of alkenes provides a useful route to CF3-containing cyclic compounds. Current approaches to generate CF3-based initiators from a CF3 source require a catalyst or an activator. This work describes a catalyst-free protocol to innately produce electrophilic CF3 species from PhICF3Cl for trifluoromethylative cyclization of acryloanilides. A new domino biscyclization of dienes has been developed leading to trifluoroethylated tetrahydroindenoquinolinones with chemo- and stereo-selectivity.
Nickel-Catalyzed Domino Heck Cyclization/Suzuki Coupling for the Synthesis of 3,3-Disubstituted Oxindoles
Li, Yuxiu,Wang, Kuai,Ping, Yuanyuan,Wang, Yifan,Kong, Wangqing
supporting information, p. 921 - 924 (2018/02/22)
The first nickel-catalyzed domino Heck cyclization/Suzuki coupling reaction for the synthesis of 3,3-disubstituted oxindoles bearing quaternary all-carbon centers is reported. A wide range of electrophiles, such as aryl iodides, bromides, triflates, and c
The carbomethylation of arylacrylamides leading to 3-ethyl-3-substituted indolin-2-one by cascade radical addition/cyclization
Dai, Qiang,Yu, Jintao,Jiang, Yan,Guo, Songjin,Yang, Haitao,Cheng, Jiang
supporting information, p. 3865 - 3867 (2014/04/03)
An FeCl2-promoted carbomethylation of arylacrylamides by di-tert-butyl peroxide (DTBP) is achieved, leading to 3-ethyl-3-substituted indolin-2-one in high yield. The reaction tolerates a series of functional groups, such as cyano, nitro, ethyloxy carbonyl, bromo, chloro, and trifluoromethyl groups. The radical methylation and arylation of the alkenyl group are involved in this reaction. This journal is the Partner Organisations 2014.
Synthesis of oxindoles through silver-catalyzed trifluoromethylation-, difluoromethylation- and arylsulfonylation-cyclization reaction of N-arylacrylamides
Liu, Jidan,Zhuang, Shaobo,Gui, Qingwen,Chen, Xiang,Yang, Zhiyong,Tan, Ze
supporting information, p. 3196 - 3202 (2014/06/09)
Efficient synthesis of trifluoromethyl and difluoromethyl-substituted oxindoles was achieved by reacting Langlois reagent or Baran reagent with N-arylacrylamides. However, the reaction of aryl sulfinic acid sodium salts with N-arylacrylamides did not give the desulfinative products, instead, aryl sulfonated products were produced. Copyright
Direct annulations toward phosphorylated oxindoles: Silver-catalyzed carbon-phosphorus functionalization of alkenes
Li, Ya-Min,Sun, Meng,Wang, Hong-Li,Tian, Qiu-Ping,Yang, Shang-Dong
supporting information, p. 3972 - 3976 (2013/05/09)
Silver screen: The AgNO3-catalyzed carbon phosphorylation of alkenes occurs by an alkene addition/cyclization cascade. Ag+ reacts with Ph2P(O)H to form the crucial active intermediate 1, which promotes the reaction. This method requires a cheap, nontoxic silver salt as the catalyst and substrates for the transformation are simple and readily accessible.
