Design and synthesis of new 1,2,4-triazole deriaties containing morpholine moiety as antimicrobial agents

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 conerted to acetohydrazide (4) ia the formation of an ester deriatie (3). Treatment of 2a and 2b with seeral 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) deriaties was performed from the reaction of 8a and 8b with substituted phenacyl bromides. All the newly synthesized compounds were screened for their antimicrobial actiities and some of them were found to possess good or moderate antimicrobial actiity. © TÜBITAK.