✦ LIBER ✦

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

✍ Scribed by V. V. Mulwad; Jyoti M. Shirodkar

Publisher: Journal of Heterocyclic Chemistry
Year: 2003
Tongue: English
Weight: 42 KB
Volume: 40
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570400231

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✦ Synopsis

Abstract

4‐Hydroxy‐2‐oxo‐2__H__‐1‐benzopyran‐3‐carboxaldehydes 2a‐d are prepared from 4‐hydroxy‐2‐oxo‐2__H__‐1‐benzopyrans 1a‐d via the Vielsmeyer Haack reaction. The 4‐hydroxy‐2‐oxo‐3‐(3′oxo‐3′‐phenylprop‐1′‐enyl)‐2__H__‐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‐2__H__‐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‐2__H__‐1‐benzopyran‐3‐aldehyde‐semicarbazone 5a‐d, which on cyclisation with ferric chloride hexahydrate gave the 5‐(4‐hydroxy‐2‐oxo‐2__H__‐1‐benzopyran‐3‐yl)‐2,4‐dihydro[1,2,4]triazol‐3‐ones 6a‐d. All these compounds show significant antibacterial activities.

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