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

共 50 条

[41] Domino Condensation/S-Arylation/Heterocyclization Reactions: Copper-Catalyzed Three-Component Synthesis of 2-N-Substituted Benzothiazoles
Ma, Dawei
Lu, Xu
Shi, Liu
Zhang, Hui
Jiang, Yongwen
Liu, Xiangqian
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (05) : 1118 - 1121
[42] Copper-catalyzed one-pot synthesis of amide linked 1,2,3-triazoles bearing aryloxy skeletons
Asgari, Mohammad Sadegh
Bahadorikhalili, Saeed
Ghaempanah, Aram
Ranjbar, Parviz Rashidi
Rahimi, Rahmatollah
Abbasi, Alireza
Larijani, Bagher
Mahdavi, Mohammad
TETRAHEDRON LETTERS, 2021, 65
[43] Copper-catalyzed CuAAC/intramolecular C-H arylation sequence: Synthesis of annulated 1,2,3-triazoles
Jeyachandran, Rajkumar
Potukuchi, Harish Kumar
Ackermann, Lutz
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2012, 8 : 1771 - 1777
[44] Copper(I)-Catalyzed Aerobic Oxidative Azide-Alkene Cycloaddition: An Efficient Synthesis of Substituted 1,2,3-Triazoles
Janreddy, Donala
Kavala, Veerababurao
Kuo, Chun-Wei
Chen, Wen-Chang
Ramesh, Chintakunta
Kotipalli, Trimurtulu
Kuo, Ting-Shen
Chen, Mei-Ling
He, Chiu-Hui
Yao, Ching-Fa
ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (14-15) : 2918 - 2927
[45] Silver-catalyzed three-component reaction: synthesis of N-substituted 1,2,3-triazoles via direct benzylic amination
Zhenhua Liu
Wenjing Hao
Wen Gao
Guangyu Zhu
Xiang Li
Lili Tong
Bo Tang
Science China(Chemistry), 2019, (08) : 1001 - 1006
[46] Direct synthesis of 2-(aminomethyl)indoles through copper(I)-catalyzed domino three-component coupling and cyclization reactions
Ohno, Hiroaki
Ohta, Yusuke
Oishi, Shinya
Fujii, Nobutaka
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (13) : 2295 - 2298
[47] Synthesis of polyfluoroaryl-containing 1,2,3-triazoles by reaction of polyfluoroarenes, sodium azide and active methylene ketones/esters
Wu, Jingjing
Fu, Dan
Cao, Song
JOURNAL OF FLUORINE CHEMISTRY, 2014, 168 : 230 - 235
[48] One-Pot Synthesis of 4-Aryl-NH-1,2,3-Triazoles through Three-Component Reaction of Aldehydes, Nitroalkanes and NaN3
Hui, Rongrong
Zhao, Mina
Chen, Ming
Ren, Zhihui
Guan, Zhenghui
CHINESE JOURNAL OF CHEMISTRY, 2017, 35 (12) : 1808 - 1812
[49] Merging decatungstate photocatalysis and copper-catalyzed azide-alkyne cycloaddition reaction for the formation of 1,2,3-triazoles in water&DAG;
Stiriba, Salah-Eddine
Aflak, Noura
El Mouchtari, El Mountassir
Ben El Ayouchia, Hicham
Rafqah, Salah
Anane, Hafid
Julve, Miguel
APPLIED ORGANOMETALLIC CHEMISTRY, 2023, 37 (08)
[50] Synthesis of 2-Arylbenzothiazoles by Copper-Catalyzed One-Pot Three-Component Reactions in Water
Xu, Hualong
Luo, Chun
Li, Zhengkai
Xiang, Haifeng
Zhou, Xiangge
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2016, 53 (04) : 1207 - 1213

← 1 2 3 4 5 →