Abstract:3-(4-amino-3-phenyl-5-thione-4,5-dihydro-1H-1,2,4-triazol-1-yl)-1,3-diphenylpropan-1-one(4) was synthesized by nucleophilic substitution of 4-amino-3-phenyl-5- mercapto-1, 2, 4-triazole and chalcone under microwave irradiation, then reacted with aryl aldehydes to give seven novel triazolethione Schiff-base derivatives(5a-5g), namely3-(4-arylimino-3-phenyl-5-thione-4,5-dihydro-1H-1,2,4-triazol-1-yl)-1,3-diphenylpropan-1-one. The influence of mole ratio of substance, the amount of catalyst, solvent, reaction time and radiant power upon the product yield was discussed. The optimal conditions for preparation were ascertained as follows: n(aromatic aldehyde): n(amino substituted triazolethione)=1:1.1, the amount of acetic acid was 2ml, the time was 5~7min, microwave power was 500W, the solvent was DMF, and the yields were 71%~87%. The structures of intermediate and target compounds were characterized by IR, MS, 1H NMR spectra and elemental analysis.