Synthesis of 1,3-diazetidin-2-ones (aza-β-lactams) as rationally designed transpeptidase and β-lactamase inhibitors

Abstract

Pyrimidinone 4 is converted to diazetidinone carboxaldehyde 6. Selective chemical transformations on tricarbonyl substrate 6 with different reagents are performed. Synthon 6 is employed as a versatile template for elaboration to bicyclic diazetidinones 7, 12 and 15. A novel class of aza-β-lactam compounds are synthesised as potential transpeptidase and β-lactamase inhibitors. © 1995 Pergamon Elsevier Science Ltd.