STEFANIA-FELICIA BARBUCEANU, GABRIEL SARAMET, GABRIELA BANCESCU, CONSTANTIN DRAGHICI, THEODORA-VENERA APOSTOL, LAURA TARAN, CRISTINA ELENA DINU-PIRVU<br>Synthesis, Characterization and Antimicrobial Activity <br>of Some Hydroxypyrazolines

STEFANIA-FELICIA BARBUCEANU, GABRIEL SARAMET, GABRIELA BANCESCU, CONSTANTIN DRAGHICI, THEODORA-VENERA APOSTOL, LAURA TARAN, CRISTINA ELENA DINU-PIRVU
Synthesis, Characterization and Antimicrobial Activity
of Some Hydroxypyrazolines

Abstract:

New hydroxypyrazolines were obtained starting from some hydrazides. 4-(4-X-Phenyl-sulfonyl)benzoic acid hydrazides 1a-c were treated with 1,1,1-trifluoroacetylacetone in order to obtain new corresponding pyrazole compounds. However, formation of desired pyrazoles from these hydrazides failed and instead new hydroxypirazolines intermediates 2a-c were obtained. Also, by reaction of 2-(5-(4-(4-chlorophenylsulfonyl)phenyl)-4-(2-fluorophenyl)-4H-1,2,4-triazol-3-ylthio)acetohydrazide 6b with 1,1,1-trifluoroacetylacetone was obtained the new hydroxypirazoline 7b and not corresponding pyrazole. The new hydrazide 6b was obtained by reaction of ethyl 2-(5-(4-(4-chlorophenylsulfonyl)phenyl)-4-(2-fluorophenyl)-4H-1,2,4-triazol-3-ylthio)acetate 5b with hydrazine hydrate. The new ester 5b was obtained by alkylation of corresponding 1,2,4-triazol-3-thione with ethyl bromoacetate in basic media. By reaction of hydrazide 1a with ethyl (4,4,4-trifluoroacetyl)acetate did not occur expected pyrazolone and the acylhydrazone intermediate 3a. The structures of these compounds were elucidated by elemental analysis and IR, UV, 1H-NMR, 13C-NMR, MS spectra. The hydroxypyrazoles obtained were tested for their antimicrobial activity. Keywords: pyrazole, hydroxypyrazoline, hydrazide, antimicrobial activity

Issue: 2013, Volume 64, Issue 4

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