Synthesis, characterization and biological activity of 1,3,4-substituted 2-azetidinones

Amido/imido alcohol/2-phenyl-3-hydroxyethylquinazolin-4 (3H) -one 1 on treatment with benzoic acid in the presence of conc. H2SO4 yields m-(aralkylamido/imidoalkyl/2-phenyl-3-ethyl-3H-4-oxoquinazolinyl) benzoic acids 2. The acid chloride of 2 on reaction with hydrazine hydrate affords m-(aralkylamido/imidoalkyl/2-phenyl-3-ethyl-3H-4-oxoquinazolinyl) benzoic acid hydrazides 4 which on condensation with an aromatic aldehyde in acetic acid gives m(aralkylamido/imidoalkyl/2-phenyl-3-ethyl-3H-4-oxo-quinazolinyl) benzoic acid hydrazones 5. Compounds 5 undergo cyclization with phenoxy acetic acid in the presence of thionyl chloride in dry benzene to furnish 1-[m(aralkylamido/imidoalkyl/2-phenyl-3-ethyl-3H-4-oxo-quinazolinyl-benzamido)]-3-phenoxy-4-phenyl-2-azetidinones 6. The antiviral and antifungal activities of 6 have been reported. IPC: Int.Cl. 7 C 07 C 59/54 // A 61 P 31/12