Switchable and efficient conversion of 2-amido-aryl oxazolines to quinazolin-4(3H)-ones and N-(2-chloroethyl)benzamides

Abstract

Switchable chemoselective conversion of 2-amido-aryl oxazolines to quinazolin-4(3H)-ones or N-(2-chloroethyl)benzamides is achieved. The former reaction is proposed to involve a PIFA-mediated 6π electrocyclization followed by an in situ nucleophilic substitution, while the latter reaction uses aluminum chloride as a halogenated source through a ring-opening reaction. The reactions proceed smoothly under mild conditions and have excellent functional group compatibility.