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(4 H )‐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(4 H )‐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 benzo[ d ]thiazole and pyrimidine‐2,4(1 H ,3 H )‐dione. Moreover, bis(oxazol‐5(4 H )‐ones) reacted with (4‐aminobenzoyl)glycine to afford bis[(4‐(5‐oxo‐1 H ‐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‐1 H ‐imidazol‐1‐yloxazol‐5(4 H )‐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.