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2024 , Vol. 44 >Issue 7: 2251 - 2256

DOI: https://doi.org/10.6023/cjoc202401030

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
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  • 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

  网络出版日期: 2024-04-25

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

  • Mengjin Liu ,
  • Yan Xiao ,
  • Kai Zhou ,
  • Zicheng Li ,
  • Wencai Huang
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  • School of Chemical Engineering, Sichuan University, Chengdu 610065
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Received date: 2024-01-24

  Revised date: 2024-03-24

  Online published: 2024-04-25

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摘要

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

本文引用格式

刘蒙金 , 肖燕 , 周锴 , 李子成 , 黄文才 . 一锅法自偶联反应合成3,5-二苯基-1,2,4-噁二唑[J]. 有机化学, 2024 , 44(7) : 2251 -2256 . DOI: 10.6023/cjoc202401030

Abstract

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

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