Preparation of anthranils via chemoselective oxidative radical cyclization of 3-(2-azidoaryl) substituted propargyl alcohols

Abstract

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.