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

✍ Scribed by Naceur Hamdi; Mustapha Saoud; Antonio Romerosa; Rached Ben Hassen

• Book ID: 102342371
• Publisher: Journal of Heterocyclic Chemistry
• Year: 2008
• Tongue: English
• Weight: 359 KB
• Volume: 45
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.5570450644

✦ Synopsis

Abstract

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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.