75670-25-6Relevant academic research and scientific papers
A Novel C–N Migration Rearrangement Based on N–F Compounds for the Synthesis of N-Alkyl Diaryl Ureas
Zhao, Yi-Xiao,Xie, Tian,Yang, San-Ke,Yang, Xian-Jin
, p. 437 - 445 (2020)
A novel rearrangement reaction based on the structure of N-fluoro-N-(phenylsulfonyl) benzamides (FPSBA) was developed. In the presence of base, unsymmetrical N-alkyl diaryl ureas were obtained in good yields which were accomplished through secondary alkyl phenylamines initiated 1,2-phenyl-shift migration rearrangement of N-fluoro-N-(phenylsulfonyl) benzamides. The reaction was carried out without using traditional, highly toxic reagents and noble metals. Whereas without rearrangement occurrence for primary phenylamines and aliphatic amines, normal amides and N-(phenylsulfonyl) benzamides were afforded respectively. Nitrene and phenyl isocyanate included process were prevented and a secondary alkyl phenylamine initiated vicinal SN2' reaction occurred. This rearrangement reaction features an interesting reaction mechanism, mild reaction conditions, simple operation, and useful products.
