Reactivity of 3-oxo-β-lactams with respect to primary amines : an experimental and computational approach

The reactivity of 3-oxo--lactams with respect to primary amines was investigated in depth. Depending on the specific azetidin-2-one C4 substituent, this reaction was shown to selectively produce 3-imino--lactams (through dehydration), -aminoamides (through CO elimination), or ethanediamides (through an unprecedented C3-C4 ring opening). In addition to the experimental results, the mechanisms and factors governing these peculiar transformations were also examined and elucidated by means of DFT calculations.