AlCl3-mediated “Heine-type” ring-opening of N-cyclopropylamides for the synthesis of 5-methyl-2-oxazolines

Abstract

A ring-opening rearrangement reaction of N-cyclopropylamides is shown to occur in the presence of AlCl₃. The mechanism proposed herein involves the “Heine-type” aziridine intermediate and C–Cl or C–O bond formation. This protocol provides quick access to N-(2-chloropropyl)amides and 5-methyl-2-oxazolines using simple and readily available starting materials.