InCl3-catalyzed 5-exo-dig cyclization/1,6-conjugate addition of N-propargylamides with p-QMs to construct oxazole derivatives

Org Biomol Chem. 2020 Mar 4;18(9):1780-1784. doi: 10.1039/c9ob02651g.

Abstract

An InCl3-catalyzed atom-economic intramolecular 5-exo-dig cyclization/1,6-conjugate addition/aromatization of N-propargylamides with p-QMs to produce oxazoles tethering diarylmethane has been successfully developed. InCl3 not only served as Lewis acid to catalyze the cyclization of propargylic amides but also activated the carbonyl of p-QMs to achieve the 1,6-addition process in a one-pot manner. The reaction has attractive features, including mild reaction conditions, broad scope of substrates, good yields, and scalability.