Tunable Synthesis of 1,2,3-Triazoles and Enamines through Deacylative Azide-Alkene Cycloaddition

被引:6
作者
Rengasamy, R. [1 ,2 ]
Raj, J. Paul [3 ]
Vijayalakshmi, K. [1 ,2 ]
Punitha, N. [1 ,2 ]
Kesavan, M. [4 ]
Vajjiravel, M. [3 ]
Elangovan, Jebamalai [1 ,2 ]
机构
[1] Rajah Serf Govt Coll, PG & Res Dept Chem, Thanjavur, India
[2] Bharathidasan Univ, Tiruchirappalli 613005 24, Tamil Nadu, India
[3] BS Abdur Rahman Crescent Inst Sci & Technol, Dept Chem, Chennai 600048, Tamil Nadu, India
[4] SRM Inst Sci & Technol, Interdisplinary Inst Indian Syst Med IIISM, Kattankulathur 603203, India
关键词
Azide-alkene cycloaddition; Cycloaddition; Deacylative azide-alkene cycloaddition; Nitrogen heterocycles; 1; 2; 3-Triazoles; RUTHENIUM-CATALYZED CYCLOADDITION; REGIOSELECTIVE SYNTHESIS; CLICK CHEMISTRY; 1,3-DIPOLAR CYCLOADDITIONS; ALKYNE CYCLOADDITION; ORGANIC AZIDES; COPPER; SCOPE; TRANSANNULATION; TRIAZOLES;
D O I
10.1002/ejoc.202101470
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A tunable synthesis of 1,4,5-trisubstituted 1,2,3-triazoles and enamines through [3+2] cycloaddition of activated olefins and organic azides is reported. Triazoles were achieved from benzylidene diketones and organic azides by copper oxide nanoparticle catalysis while enamines were synthesized from benzylidene malonates and organic azides under solvent-free and catalyst-free condition.
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页数:5
相关论文
共 76 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]   Copper Catalysis and Organocatalysis Showing the Way: Synthesis of Selenium-Containing Highly Functionalized 1,2,3-Triazoles [J].
Alves, Diego ;
Goldani, Bruna ;
Lenardao, Eder J. ;
Perin, Gelson ;
Schumacher, Ricardo F. ;
Paixao, Marcio W. .
CHEMICAL RECORD, 2018, 18 (05) :527-542
[3]  
[Anonymous], 2002, Angew. Chem, V114, P2708
[4]  
[Anonymous], 2012, Angew. Chem, V124, P886
[5]  
[Anonymous], 2014, ANGEW CHEM, V126, P10588
[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]  
Borgati T.F., 2013, CHEM SOC REV, V24, P6
[9]  
Bozorov K., 2019, BIOORGAN MED CHEM, V15, P27
[10]   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