Efficient synthesis and characterization of novel bis-heterocyclic derivatives and benzo-fused macrocycles containing oxazolone or imidazolone subunits

Bis(3-(arylthiomethyl)benzaldehydes), linked to aliphatic spacers via ethers, were prepared and used as key synthons for the bis(2-phenyloxazol-5(4H)-ones) via their reaction with benzoylglycine in acetic anhydride in the presence of fused sodium acetate at 100°C for 6 hours. Bis(oxazol-5(4H)-ones) were reacted with the appropriate aromatic or heterocyclic amines in glacial acetic acid in the presence of fused sodium acetate at 100°C for 24 hours to afford a novel series of bis(2-phenylimidazol-4-ones) and their related hybrids with benzod]thiazole and pyrimidine-2,4(1H,3H)-dione. Moreover, bis(oxazol-5(4H)-ones) reacted with (4-aminobenzoyl)glycine to afford bis(4-(5-oxo-1H-imidazol-1-yl)benzoyl)glycine] derivatives followed by their reaction with anisaldehyde in acetic anhydride containing fused sodium acetate at 100°C for 12 hours to afford bis(5-oxo-1H-imidazol-1-yloxazol-5(4H)-one) hybrids. Furthermore, bis(3-(arylthiomethyl)benzaldehydes) were reacted with 2,2′-(terephthaloylbis(azanediyl))diacetic acid in acetic anhydride containing fused sodium acetate at 100°C for 12 hours to give benzo-fused macrocycles containing oxazolone subunits which reacted with appropriate aromatic amines in DMF and glacial acetic acid containing fused sodium acetate at 100°C for 24 hours to give benzo-fused macrocycles containing imidazolone subunits.