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Synthesis, spectroscopic and antibacterial investigations of new hydroxy ethers and heterocyclic coumarin derivatives
Author(s) -
Hamdi Naceur,
Saoud Mustapha,
Romerosa Antonio,
Hassen Rached Ben
Publication year - 2008
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.5570450644
Subject(s) - chemistry , coumarin , moiety , two dimensional nuclear magnetic resonance spectroscopy , yield (engineering) , nuclear magnetic resonance spectroscopy , stereochemistry , antibacterial activity , carbon 13 nmr , proton nmr , organic chemistry , bacteria , materials science , biology , metallurgy , genetics
The reactions between oligoethylene glycol diglycidyl ethers 2a‐c with both 7‐hydroxy‐4‐methyl‐2 H ‐chromen‐2‐one and 4‐hydroxy‐2 H ‐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‐2 H ‐chromen‐2‐one 5 and new heterocyclic compounds 4‐hydroxy‐3‐(1 H ‐pyrazol‐3‐yl)‐2 H ‐chromen‐2‐one 6a , 4‐hydroxy‐3‐(1‐phenylpyrazol‐3‐yl)‐2 H ‐chromen‐2‐one 6b and 4‐hydroxy‐3‐(isoxazol‐3‐yl)‐2 H ‐chromen‐2‐one 6c is also described. All compounds were characterized by 1 H NMR, 13 C{ 1 H} NMR, 2D‐ 1 H‐ 13 C HMBC, 2D‐ 1 H 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.