114126-86-2Relevant academic research and scientific papers
Tertiary amines as synthetic equivalents of vinyl cations: Zinc bromide promoted coupling of propargylamines with α-isocyanoacetamides to give 2,4,5-trisubstituted oxazoles initiated by an internal redox process
Odabachian, Yann,Wang, Qian,Zhu, Jieping
, p. 12229 - 12233 (2013)
Crabee interrupted: Propargylamines 1 react with α-isocyanoacetamides 2 in the presence of zinc bromide to afford vinyl oxazoles 3. The transformation, wherein the propargylamine acts as a vinyl cation synthetic equivalent, involves a domino sequence incorporating a 1,5-hydride shift, intermolecular trapping/cyclization, and a 1,6-elimination (see scheme). Copyright
