Further observations on the rearrangement of 3-acylaminoazetidinones

Abstract

In addition to formation of 3-benzoyl-1,2-diphenylimidazolid-5-one, acid-catalysed rearrangement of 3-benzamido-1,4-diphenylazetidin-2-one yields 4-benzylidene-2-phenyloxazol-5-one, 4-benzylidene-1,2-diphenylimidazol-5-one, α-benzamidocinnamanilide and hippuranilide. The effect on the distribution of products of replacing phenyl groups of the azetidinone by other aryl groups has been examined, and correlated with possible rearrangement mechanisms.