微波辐射下1,2,4-三唑硫酮席夫碱的合成及表征  

Synthesis of 1,2,4-Triazole Thioketone Schiff-bases Under Microwave Irradiation and Its Characterization

作　　者：高妍[1,2] 宋健[1] 王伟[3] 

机构地区：[1]天津大学化学工程学院,天津300072 [2]辽宁科技大学化学工程学院,辽宁鞍山114004 [3]上海应用技术学院香料香精技术与工程学院,上海200235

出　　处：《精细化工》2012年第5期482-486,共5页Fine Chemicals

基　　金：辽宁省教育厅重点实验室项目(2008S127);辽宁省科技厅博士启动基金项目(05L003)~~

摘　　要：微波辐射条件下,以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3-(4-氨基-5-硫基-3-苯基均三唑-1-氮代)-1,3-二苯-1-丙酮(Ⅳ),Ⅳ与系列芳香醛经缩合反应,合成了7种三唑硫酮席夫碱Ⅴa～Ⅴg。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(芳香醛)∶n(氨基三唑硫酮)=1∶1.1,微波功率500 W,催化剂冰醋酸2 mL,反应时间5～7 min,溶剂为N,N-二甲基甲酰胺(DMF),收率为71%～87%。用IR、MS、1HNMR、元素分析对合成中间体和目标产物进行了结构表征。3-（4-Amino-3-phenyl-5-thioxo-4,5-dihydro-1H-1,2,4-triazol-1-yl）-1,3-diphenylpropanal（Ⅳ） was synthesized by nucleophilic substitution of 4-amino-3-phenyl-5-mercapto-1,2,4-triazole and chalcone under microwave irradiation.The product then reacted with aryl aldehydes to give seven novel triazolethione Schiff-base derivatives（Ⅴa~Ⅴg）,namely,3-[4-（arylideneamino）-3-phenyl-5-thioxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-1,3-diphenylpropanal.The influence of mole ratio of substrate,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 2 mL,the time 5～7 min,microwave power 500 W,the solvent DMF,and the yields were 71%～87%.The structures of the intermediate and the target compounds were characterized by means of IR,MS,1HNMR spectra and elemental analysis.

关 键 词：微波 三唑硫酮 席夫碱 医药与日化原料 

分 类 号：O625.63[理学—有机化学]