1007638-91-6Relevant academic research and scientific papers
Synthesis of bicyclic imidazoles via [2 + 3] cycloaddition between nitriles and regioselectively generated α-imino gold carbene intermediates
Xiao, Yuanjing,Zhang, Liming
, p. 4662 - 4665 (2012)
The cyclic α-imino gold carbene intermediate B is most likely generated in situ via regioselective nitrene transfer from an azido group to a tethered terminal alkyne in the presence of a gold catalyst and at ambient temperature. This highly electrophilic intermediate can react with a weakly nucleophilic nitrile, which is used as the reaction solvent, to deliver a bicyclic imidazole rapidly in an overall bimolecular [2 + 2 + 1] cycloaddition and in mostly serviceable yield. The competing intramolecular Huisgen reaction, although likely also catalyzed by gold, is minimized by using AuCl3 as the catalyst.
