有机化学 ›› 2024, Vol. 44 ›› Issue (7): 2251-2256.DOI: 10.6023/cjoc202401030 上一篇    下一篇

研究论文

一锅法自偶联反应合成3,5-二苯基-1,2,4-噁二唑

刘蒙金, 肖燕, 周锴, 李子成*(), 黄文才   

  1. 四川大学化学工程学院 成都 610065
  • 收稿日期:2024-01-24 修回日期:2024-03-24 发布日期:2024-04-24

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

Mengjin Liu, Yan Xiao, Kai Zhou, Zicheng Li(), Wencai Huang   

  1. School of Chemical Engineering, Sichuan University, Chengdu 610065
  • Received:2024-01-24 Revised:2024-03-24 Published:2024-04-24
  • Contact: E-mail: sculzc@scu.edu.cn

开发了一种合成1,2,4-噁二唑的新方法. 在Cs2CO3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-噁二唑, 自偶联反应, 醛类, 氯苯甲醛肟, 环化反应

3,5-Diaryl-1,2,4-oxadiazoles were synthesized by homocoupling of chloroarylaldoxime from arylaldoxime and N-chlorosuccinimide (NCS) in the presence of Cs2CO3 in one pot. The method is suitable for thiophene-3-carbaldehyde, isonicotinaldehyde 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 carboxylic acid). Compared to reported methods, this method uses only aromatic aldoxime as a single substrate. The process is simple, convenient, and green, making it a reliable way to synthesize 3,5-(homo-substituted)-1,2,4-oxadiazoles.

Key words: 1,2,4-oxadiazole, homocoupling reaction, aldehydes, chlorobenzaldoxime, cyclic addition