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Synthesis anti‐fungal and anti‐bacterial screening of 3‐phenyl‐1,4,5‐trihydro‐pyrazol and 2, 4‐dihydro[ 1,2,4]‐triazol‐3‐one derivatives of 4‐hydroxy‐2‐oxo‐2H‐1‐benzopyran
Authors:V V Mulwad  Jyoti M Shirodkar
Abstract:4‐Hydroxy‐2‐oxo‐2H‐1‐benzopyran‐3‐carboxaldehydes 2a‐d are prepared from 4‐hydroxy‐2‐oxo‐2H‐1‐benzopyrans 1a‐d via the Vielsmeyer Haack reaction. The 4‐hydroxy‐2‐oxo‐3‐(3′oxo‐3′‐phenylprop‐1′‐enyl)‐2H‐1‐benzopyrans 3a‐d are obtained from 2a‐d via the Claisen reaction. Refluxing compounds 3a‐d with hydrazine hydrate gave the 3‐phenyl‐5‐(4‐hydroxy‐2‐oxo‐2H‐1‐benzopyran‐3‐yl)‐1,4,5‐trihydropyra‐zols 4a‐d . Stirring compounds 2a‐d with semicarbazide hydrochloride in acidic medium gave the 4‐hydroxy‐2‐oxo‐2H‐1‐benzopyran‐3‐aldehyde‐semicarbazone 5a‐d , which on cyclisation with ferric chloride hexahydrate gave the 5‐(4‐hydroxy‐2‐oxo‐2H‐1‐benzopyran‐3‐yl)‐2,4‐dihydro1,2,4]triazol‐3‐ones 6a‐d . All these compounds show significant antibacterial activities.
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