Synthesis of 3,5-Diaryl-1,2,4-oxadiazole by One-Pot Homocoupling Reaction  

一锅法自偶联反应合成3,5-二苯基-1,2,4-噁二唑

作　　者：Liu Mengjin Xiao Yan Zhou Kai Li Zicheng Huang Wencai 刘蒙金;肖燕;周锴;李子成;黄文才(四川大学化学工程学院,成都610065)

机构地区：[1]School of Chemical Engineering,Sichuan University,Chengdu 610065

出　　处：《有机化学》2024年第7期2251-2256,共6页Chinese Journal of Organic Chemistry

摘　　要：3,5-Diaryl-1,2,4-oxadiazoles were synthesized by homocoupling of chloroarylaldoxime from arylaldoxime and N-chlorosuccinimide(NCS)in the presence of Cs_(2)CO_(3) in one pot.The method is suitable for thiophene-3-carbaldehyde,ison-icotinaldehyde and arylaldehyde without active substituent with a yield from 19%to 78%.However,it was not suitable for aliphatic aldehydes,other heteroaromatic aldehydes and benzaldehydes carrying active groups(hydroxyl,amino and carbox-ylic acid).Compared to reported methods,this method uses only aromatic aldoxime as a single substrate.The process is sim-ple,convenient,and green,making it a reliable way to synthesize 3,5-(homo-substituted)-1,2,4-oxadiazoles.开发了一种合成1,2,4-噁二唑的新方法.在Cs_(2)CO_(3)存在下,以苯甲醛肟和N-氯代丁二酰亚胺(NCS)为原料,采用一锅法自偶联反应合成了3,5-二苯基-1,2,4-噁二唑.该方法适用于无活性取代基的噻吩-3-甲醛、异烟醛和苯甲醛,产率为19%~78%;但该方法不适用于脂肪族醛、其他杂芳香族醛和带有活性基团(羟基、氨基和羧酸)的苯醛.相比于其他方法,此方法底物单一,仅为芳香醛肟,过程简单,符合绿色化学理念,是合成3,5-(同取代基)-1,2,4-噁二唑的便捷方法.

关 键 词：1 2 4-oxadiazole homocoupling reaction ALDEHYDES chlorobenzaldoxime cyclic addition 

分 类 号：O626[理学—有机化学]