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
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
收藏
页码:3105 / 3108
页数:4
相关论文
共 64 条
[1]   Click Chemistry: 1,2,3-Triazoles as Pharmacophores [J].
Agalave, Sandip G. ;
Maujan, Suleman R. ;
Pore, Vandana S. .
CHEMISTRY-AN ASIAN JOURNAL, 2011, 6 (10) :2696-2718
[2]   Synthesis of 4-aryl-1H-1,2,3-triazoles through TBAF-catalyzed [3+2] cycloaddition of 2-aryl-1-nitroethenes with TMSN3 under solvent-free conditions [J].
Amantini, D ;
Fringuelli, F ;
Piermatti, O ;
Pizzo, F ;
Zunino, E ;
Vaccaro, L .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (16) :6526-6529
[3]   HIGH-PRESSURE INDUCED 1,3-DIPOLAR CYCLOADDITIONS OF AZIDES WITH ELECTRON-DEFICIENT OLEFINS [J].
ANDERSON, GT ;
HENRY, JR ;
WEINREB, SM .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (24) :6946-6948
[4]  
[Anonymous], 10356983A CCDC
[5]   Synthesis and polymerization of C-vinyl- and N-vinyl-1,2,3-triazoles [J].
Beghdadi, Samir ;
Miladi, Imen Abdelhedi ;
Addis, Daniele ;
Ben Romdhane, Hatem ;
Bernard, Julien ;
Drockenmuller, Eric .
POLYMER CHEMISTRY, 2012, 3 (07) :1680-1692
[6]   Organocatalytic Synthesis of 1,2,3-Triazoles from Unactivated Ketones and Arylazides [J].
Belkheira, Mokhtaria ;
El Abed, Douniazad ;
Pons, Jean-Marc ;
Bressy, Cyril .
CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (46) :12917-12921
[7]   Ruthenium-catalyzed azide-alkyne cycloaddition: Scope and mechanism [J].
Boren, Brant C. ;
Narayan, Sridhar ;
Rasmussen, Lars K. ;
Zhang, Li ;
Zhao, Haitao ;
Lin, Zhenyang ;
Jia, Guochen ;
Fokin, Valery V. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (28) :8923-8930
[8]   CYCLOADDITION REACTIONS OF AZIDES WITH ELECTRON-POOR OLEFINS - ISOMERIZATION AND THERMOLYSIS OF RESULTING DELTA-2-TRIAZOLINES [J].
BROECKX, W ;
OVERBERG, N ;
SAMYN, C ;
SMETS, G ;
LABBE, G .
TETRAHEDRON, 1971, 27 (15) :3527-+
[9]   Transition-Metal-Catalyzed Denitrogenative Transannulation: Converting Triazoles into Other Heterocyclic Systems [J].
Chattopadhyay, Buddhadeb ;
Gevorgyan, Vladimir .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (04) :862-872
[10]   Copper-Catalyzed [3+2] Cycloaddition/Oxidation Reactions between Nitro-olefins and Organic Azides: Highly Regioselective Synthesis of NO2-Substituted 1,2,3-Triazoles [J].
Chen, Yunfeng ;
Nie, Gang ;
Zhang, Qi ;
Ma, Shan ;
Li, Huan ;
Hu, Qinquan .
ORGANIC LETTERS, 2015, 17 (05) :1118-1121