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

被引：0

作者：

Liu Mengjin ^{[1
]}

Xiao Yan ^{[1
]}

Zhou Kai ^{[1
]}

Li Zicheng ^{[1
]}

Huang Wencai ^{[1
]}

机构：

[1] Sichuan Univ, Sch Chem Engn, Chengdu 610065, Peoples R China

来源：

CHINESE JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 44卷 / 07期

关键词：

1,2,4-oxadiazole; homocoupling reaction; aldehydes; chlorobenzaldoxime; cyclic addition; 3,5-DISUBSTITUTED 1,2,4-OXADIAZOLES; EFFICIENT SYNTHESIS; NITRILE; CYCLOADDITIONS; FLUORIDE;

D O I：

10.6023/cjoc202401030

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

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 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.

引用

页码：2251 / 2256

页数：6

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