Synthesis and characterization of 1,2,4-tiazoles consisting of 4-methoxyphenyl and 4-hydroxyphenyl

In this study, novel 9 compounds 4-(4-methoxyphenylethyl)-5-2H-1,2,4-triazol-3(4H)-one (51), 5-ethyl-4-(4-methoxyphenylethyl)-2H-1,2,4-triazol-3(4H)-one (52), 4-(4-methoxyphenylethyl)-5-propyl-2H-1,2,4-triazol-3(4H)-one (53), 4-(4-methoxyphenylethyl) -5-(thiophen-2-ylmethyl)-2H-1,2,4-triazol-3(4H)-one (54), 5-benzyl-4-(4-methoxyphenylethyl)-2H-1,2,4-triazol-3(4H)-one (55), 5-(4-bromobenzyl)-4-(4-methoxyphenylethyl)-2H-1,2,4-triazol-3(4H)-one (56), 4-(4-methoxypheylethyl)-5-(4-nitrobenzyl)-2H-1,2,4-triazol-3(4H)-one (57), 4-(4-methoxyphenylethyl)-5-p-tolyl-2H-1,2,4-triazol-3(4H)-on (58), 5-(4-chlorobenzyl)-4-(4-methoxyphenylethyl)-2H-1,2,4-triazol-3(4H)-one (59) were synthesized from reaction 2-(4-methoxyphenyl)ethylamine and a series of ester ethoxy carbonyl hydrazones. Some of these compounds were treated with BBr3 to obtain novel 5 cathechol containing compounds namely, 4-(4-hydroxyphenylethyl)-5-methyl-2H-1,2,4-triazol-3(4H)-one (61), 5-ethyl-4-(4-hydroxyphenylethyl)-2H-1,2,4-triazol-3(4H)-one (62), 4-(4-hydroxyphenylethyl)-5-propyl-2H-1,2,4-triazol-3(4H)-one (63), 4-(4-hydroxyphenylethyl)-5-( thiophen -2-ylmethyl)-2H-1,2,4-triazol-3(4H)-one (64), 5-benzyl-4-(4-hydroxyphenylethyl)-2H-1,2,4-triazol-3(4H)-one (65).Compounds were though that contain catechol character were tested for their antioxidant and antimicrobial properties however all of them gave negative results for antioxidant activities. It?s determineted that antimicrobial activites 58 and 64 number compounds.The structure of 14 novel compounds synthesized in this study were analyzed by IR, 1H-NMR & 13C-NMR spectroscopy and reaction mechanisms were proposed for the general sythesis.