Preparation Of Anthranils Via Chemoselective Oxidative Radical Cyclization Of 3-(2-Azidoaryl) Substituted Propargyl Alcohols

In the presence of K2S2O8 and HOAc, 3-(2-azidoaryl) substituted propargyl alcohols can go through chemoselective oxidative radical cyclizations to give a pool of anthranils based on Meyer-Schuster rearrangement. It's proposed that the cyclizations were triggered exclusively by the direct attack of oxygen radicals on the azides. The weak N-O bonds in anthranils could be easily cleaved in the presence of transition metal catalysts and went through aminations with 2-oxo-2-phenylacetic acid and iodobenzene.