微波辐射下1, 2, 4-三唑硫酮席夫碱衍生物的合成及表征

Synthesis and Characterization of the Derivatives of 1,2,4-Triazole Thioketone Schiff-base under Microwave Irradiation

摘要:

微波辐射条件下，以自制的氨基均三唑硫醇与查尔酮为原料, 通过亲核取代反应，制备了氨基均三唑氮代二苯丙酮(4)，(4)与系列芳香醛经缩合反应合成了7种未见文献报道的三唑硫酮席夫碱5a~5g。探讨了原料摩尔比、催化剂用量、反应时间、溶剂、微波辐射功率对收率的影响，得到了优化的工艺条件：n(芳醛): n(氨基三唑硫酮)=1:1，微波功率500 W，催化剂冰醋酸2ml，反应时间5~7min，溶剂为DMF, 收率为71%~87%。利用IR、MS、1H NMR、元素分析对合成中间体和目标产物进行了结构表征。

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．