Microwave-assisted rapid synthesis of α-amino-β-lactams

Article abstract of DOI:10.1016/0040-4039(96)01571-7

A rapid and convenient approach to α-amino-β-lactams has been developed using the tetrachlorophthalimido group as a masked amino substituent. Reaction between glycine and tetrachlorophthalic anhydride in DMF for about 90 sec in a domestic microwave oven led to an imidoacetic acid in high yield; the corresponding acid chloride reacted with Schiff bases to provide mixtures of trans and cis β-lactams. Nearly exclusive formation of trans β-lactams could be achieved in some cases in a few minutes by conducting β-lactam formation under strong microwave irradiation. Facile conversion to α-amino-β-lactams was realized in 5-10 minutes via solventless reaction of these α-amino-β-lactams with ethylenediamine at room temperature.