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

Abstract

(Chemical Equation Presented) 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 to 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-chomen-2-one 6a, 4-hydoxy-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.