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Efficient synthesis and characterization of novel bis‐heterocyclic derivatives and benzo‐fused macrocycles containing oxazolone or imidazolone subunits
Author(s) -
Sanad Sherif M. H.,
Mekky Ahmed E. M.
Publication year - 2020
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.4102
Subject(s) - chemistry , acetic anhydride , acetic acid , oxazolone , synthon , sodium acetate , sodium ethoxide , thiazole , sodium , medicinal chemistry , organic chemistry , stereochemistry , catalysis , ethanol
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.