A tunable route to oxidative and eliminative [3+2] cycloadditions of organic azides with nitroolefins: CuO nanoparticles catalyzed synthesis of 1,2,3-triazoles under solvent-free condition

被引：36

作者：

Gangaprasad, D. ^{[1
]}

Raj, J. Paul ^{[1
]}

Kiranmye, T. ^{[1
]}

Sasikala, R. ^{[1
]}

Karthikeyan, K. ^{[1
]}

Rani, S. Kutti ^{[1
]}

Elangovan, J. ^{[2
]}

机构：

[1] BS Abdur Rahman Univ, Dept Chem, Seethakathi Estate, Madras 600048, Tamil Nadu, India

[2] HH Rajahs Coll, Dept Chem, Pudukkottai 622001, Tamil Nadu, India

来源：

TETRAHEDRON LETTERS | 2016年 / 57卷 / 29期

关键词：

3+2] cycloaddition; Azide-olefin; CuO nanoparticles; Solvent-free condition; Catalyst recyclability; CLICK CHEMISTRY; REGIOSELECTIVE SYNTHESIS; 1,3-DIPOLAR CYCLOADDITIONS; EFFICIENT SYNTHESIS; BRONSTED ACID; TRIAZOLE; ALKYNES; TRANSANNULATION; CONSTRUCTION; LIGATION;

D O I：

10.1016/j.tetlet.2016.06.004

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A regioselective and tunable synthesis of 1,5-disubstituted 1,2,3-triazloles from oxidative and eliminative [3+2] cycloadditions of nitroolefins and organic azides under solvent-free condition in the presence and absence of commercially available CuO nanoparticle catalyst is described. In the presence of the catalyst under solvent-free condition, nitro group is retained in the product while it gets eliminated in the absence of the catalyst. (C) 2016 Elsevier Ltd. All rights reserved.

引用

页码：3105 / 3108

页数：4

共 64 条

[61] Ruthenium-catalyzed cycloaddition of alkynes and organic azides [J].

Zhang, L ;

Chen, XG ;

Xue, P ;

Sun, HHY ;

Williams, ID ;

Sharpless, KB ;

Fokin, VV ;

Jia, GC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (46) :15998-15999

[62] CuO-Promoted Construction of N-2-Aryl-Substituted-1,2,3-Triazoles via Azide-Chalcone Oxidative Cycloaddition and Post-Triazole Arylation [J].

Zhang, Yuanqing ;

Li, Xiaolong ;

Li, Jihui ;

Chen, Jinying ;

Meng, Xu ;

Zhao, Mingming ;

Chen, Baohua .

ORGANIC LETTERS, 2012, 14 (01) :26-29

[63] Stabilized Copper(I) Oxide Nanoparticles Catalyze Azide-Alkyne Click Reactions in Water [J].

Zhang, Zhenfang ;

Dong, Changming ;

Yang, Cuihong ;

Hu, Di ;

Long, Jing ;

Wang, Ling ;

Li, He ;

Chen, Yue ;

Kong, Deling .

ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (10) :1600-1604

[64]

Zhou X, 1886, EUR J ORG CHEM, P2016

← 1 2 3 4 5 6 7 →