3900-46-7Relevant academic research and scientific papers
Radical Beckmann Rearrangement and Its Application in the Formal Total Synthesis of Antimalarial Natural Product Isocryptolepine via C-H Activation
Mahajan, Pankaj S.,Humne, Vivek T.,Tanpure, Subhash D.,Mhaske, Santosh B.
supporting information, p. 3450 - 3453 (2016/07/26)
The Beckmann rearrangement of ketoximes, mediated by ammonium persulfate-dimethyl sulfoxide as a reagent, has been achieved under neutral conditions. Based on the radical trapping and 18O-labeling experiments, the transformation follows a mechanism involving a radical pathway. The scope and generality of the developed protocol has been demonstrated by 19 examples. The developed protocol and Pd-catalyzed intramolecular double C-H activation were used as key steps in the formal total synthesis of antimalarial natural product isocryptolepine.
Lewis acid-assisted N-fluorobenzenesulfonimide-based electrophilic fluorine catalysis in Beckmann rearrangement
Xie, Fukai,Du, Chuan,Pang, Yadong,Lian, Xu,Xue, Chentao,Chen, Yanyu,Wang, Xuefei,Cheng, Maosheng,Guo, Chun,Lin, Bin,Liu, Yongxiang
, p. 5820 - 5824 (2016/12/06)
A microwave-assisted N-fluorobenzenesulfonimide (NFSI)/Lewis acid-catalyzed Beckmann rearrangement was developed. The remarkable promotion to the electrophilicity of NFSI by Lewis acids was illustrated utilizing a series of readily available oxime substrates. The action model between NFSI and Lewis acids was probed by control experiments and theoretical calculations.
Schmidt reaction of ketones in dme solution in a continuous-flow microreactor
Chen, Yuesu,Liu, Binjie,Liu, Xiaofeng,Yang, Yongtai,Ling, Yun,Jia, Yu
supporting information, p. 1589 - 1592 (2015/02/19)
The Schmidt reaction, the treatment with hydroazoic acid in the presence of a strong acid, converts ketones to amides directly and has been broadly applied in organic synthesis. In this communication, the Schmidt reaction of ketones was carried out in DME solution in a continuous-flow microreactor and gave the amide products. The enclosed small-volume feature of the microreactor made this reaction safe, fast, and cost-effective.
