- Turkish Journal of Chemistry
- Vol: 36 Issue: 3
- Design and synthesis of new 1,2,4-triazole derivatives containing morpholine moiety as antimicrobial...
Design and synthesis of new 1,2,4-triazole derivatives containing morpholine moiety as antimicrobial agents
Authors : Deniz Şahin, Hacer Bayrak, Ahmet Demirbaş, Neslihan Demirbaş
Pages : 411-426
Doi:10.3906/tar-1210-28
View : 13 | Download : 7
Publication Date : 9999-12-31
Article Type : Makaleler
Abstract :2-Morpholine-4ylethyl-3H-1,2,4-triazole-3-ones (2a, 2b) were obtained from the condensation between the corresponding ethoxycarbonylhydrazones and 2-morpholinoethanamine. 2a was converted to acetohydrazide (4) via the formation of an ester derivative (3). Treatment of 2a and 2b with several aryl sulfonyl chlorides afforded the corresponding 2-arylsulfonyl-1,2,4-triazole-3-ones (5a-c and 6). The reaction of hydrazide (4) with benzyl iso- and benzyl isothiocyanate produced the corresponding carboxamide (8a) and carbothioamide (8b). The basic treatment of 8b yielded 5-mercapto-4H-1,2,4-triazol-3-yl)methyl]-2,4-dihydro-3H-1,2,4-triazol-3-one (10). The synthesis of 1,3-thiazol-2(3H)-ylidene-1,2,4-triazol-1- ylacetohydrazide (11) and 1,3-oxazole-2(3H)-ylidene-1,2,4-triazole- 1-yl)acetohydrazide (9) derivatives was performed from the reaction of 8a and 8b with substituted phenacyl bromides. All the newly synthesized compounds were screened for their antimicrobial activities and some of them were found to possess good or moderate antimicrobial activity.Keywords : 1, 2, 4-Triazole, 1, 3-oxazole, 1, 3-thiazole, morpholine, antimicrobial activity