Synthesis and Characterizations of Some New 4H-1,2,4-Triazole Derivatives (original) (raw)

3-[(5-Amino-1,3,4-thiadiazol-2-yl)methyl]-4-ethoxycarbonylamino-5-alkyl-4H-1,2,4-triazoles (2a,b) were obtained from the reaction of 3-cyanomethyl-5-alkyl-4-ethoxycarbonylamino-4H-1,2,4-triazoles (1a,b) with thiosemicarbazide in the presence of trifluoroacetic acid. The treatment of the obtained compounds (2a,b) with acetic anhydride for 1 h afforded 3-[(5-acetylamino-1,3,4-thiadiazol-2-yl)methyl]4-ethoxycarbonylamino-5-alkyl-4H-1,2,4-triazoles (3a,b). The synthesis of 4-ethoxycarbonylamino-3[(2,3-dihydro-1,3-benzoxazol-2-yl)methyl]-5-(4-methylbenzyl)-4H-1,2,4-triazole (4) was performed by the treatment of 3-[(5-acetylamino-1,3,4-thiadiazol-2-yl)methyl]-4-ethoxycarbonylamino-5-(4-methylbenzyl)4H-1,2,4-triazole (3a) with o-aminophenol under nitrogen atmosphere for 50 h. The reaction of compounds 1a,b with salicylaldehyde in the presence of sodium ethoxide yielded 2-{4-[(ethoxycarbonyl)amino]5-alkyl-4H-1,2,4-triazol-3-yl}-3-(2-hydroxyphenyl)-acrylonitriles (5a,b). The acetylations of ...