Synthesis of 2,1-Benzoisoxazole-Containing 1,2,3-Triazoles through Copper-Catalyzed Three-Component Domino Reactions of o-Bromoacetophenones, Aldehydes, and Sodium Azide

被引：21

作者：

Wang, Yuwei ^{[1
]}

Yu, Pei ^{[1
]}

Ren, Qingyun ^{[2
]}

Jia, Fengcheng ^{[1
]}

Chen, Yunfeng ^{[1
]}

Wu, Anxin ^{[3
]}

机构：

[1] Wuhan Inst Technol, Wuhan, Hubei, Peoples R China

[2] HEC Pharma Grp, Dongguan, Peoples R China

[3] Cent China Normal Univ, Wuhan, Hubei, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 85卷 / 04期

基金：

中国国家自然科学基金;

关键词：

ONE-POT SYNTHESIS; N BOND FORMATION; REGIOSELECTIVE SYNTHESIS; MULTICOMPONENT SYNTHESIS; C-N; CYCLOADDITION; CONDENSATION; ALKYNES; NITROALKANES; NITROOLEFINS;

D O I：

10.1021/acs.joc.9b02865

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We herein describe an efficient copper-catalyzed three-component domino protocol used to prepare 2,1-benzoisoxazole-containing 1,2,3-triazoles from commercially available o-bromoacetophenones, aldehydes, and sodium azide. This domino process involves Aldol condensation, copper-catalyzed azide-chalcone oxidative cyclization, 1,2,3-triazole-assisted azidation, and denitrogenative cyclization sequences. The formed compounds could be considered as benzo[c]isoxazole-functionalized combretastatin A-4 triazole analogues, which might be potential applications in the discovery of a new anticarcinogen.

引用

页码：2688 / 2696

页数：9

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