Reaction of oxazolines with phosphorus oxychloride

Abstract

The reaction of simple aryloxazolines with phosphorus oxychloride in pyridine affords aryl nitriles. Alcohols, obtained by the reaction of ortho-lithiated oxazolines with ketones, under similar conditions, typically give substituted aryl nitriles. Exceptionally, further reaction can afford substituted indenone derivatives. Alcohols obtained by the reaction of ortho-lithiated oxazolines with aryl aldehydes react with phosphorus oxychloride in pyridine to give products by cleavage of the oxazoline ring.