MICROWAVE-ASSISTED RAPID SYNTHESIS OF ALPHA-AMINO-BETA-LACTAMS

A rapid and convenient approach to alpha-amino-beta-lactams has been d eveloped using the tetrachlorophthalimido group as a masked amino subs tituent Reaction between glycine and tetrachlorophthalic anhydride in DMF for about 90 sec in a donrestic microwave oven led to an imidoacet ic acid in high yield; the corresponding acid chloride reacted with Sc hiff bases to provide mixtures of trans and cis beta-lactams Nearly ex clusive formation of trans beta-lactams could be achieved in some case s in a few minutes by conducting beta-lactam formation under strong mi crowave irradiation. Facile conversion to alpha-amino-beta-lactams was realized in 5-10 minutes via solventless reaction of these alpha-amin o-beta-lactams with ethylenediamine at room temperature. Copyright (C) 1996 Elsevier Science Ltd