Synthesis, spectroscopic and antibacterial investigations of new hydroxy ethers and heterocyclic coumarin derivatives

Abstract magnified image The reactions between oligoethylene glycol diglycidyl ethers 2a‐c with both 7‐hydroxy‐4‐methyl‐2H‐chromen‐2‐one and 4‐hydroxy‐2H‐chromen‐2‐one lead to new hydroxy ethers 3 and 4 containing coumarin moieties in good yield. The synthesis of 3‐(3‐(dimethylamino)acryloyl)‐4‐hydroxy‐2H‐chromen‐2‐one 5 and new heterocyclic compounds 4‐hydroxy‐3‐(1H‐pyrazol‐3‐yl)‐2H‐chromen‐2‐one 6a, 4‐hydroxy‐3‐(1‐phenylpyrazol‐3‐yl)‐2H‐chromen‐2‐one 6b and 4‐hydroxy‐3‐(isoxazol‐3‐yl)‐2H‐chromen‐2‐one 6c is also described. All compounds were characterized by 1H NMR, 13C{1H} NMR, 2D‐1H‐13C HMBC, 2D‐1H NOESY NMR, IR, and MS spectroscopy. Additionally, the antibacterial activity of the new products containing coumarin moiety was evaluated. This activity is clearly dependent on the chemical structure of compounds.