Organocatalytic routes toward substituted 1,2,3-triazoles

被引：147

作者：

John, Jubi ^{[1
]}

Thomas, Joice ^{[1
]}

Dehaen, Wim ^{[1
]}

机构：

[1] Katholieke Univ Leuven, Dept Chem, Mol Design & Synth, B-3001 Leuven, Belgium

来源：

CHEMICAL COMMUNICATIONS | 2015年 / 51卷 / 54期

关键词：

AZIDE-ALKYNE CYCLOADDITION; RUTHENIUM-CATALYZED CYCLOADDITION; FREE CLICK CHEMISTRY; METAL-FREE SYNTHESIS; 1,3-DIPOLAR CYCLOADDITION; REGIOSELECTIVE SYNTHESIS; AZIDOPHENYL ARYLSELENIDES; REGIOSPECIFIC SYNTHESIS; TRIAZOLE FORMATION; DIRECT ACCESS;

D O I：

10.1039/c5cc02319j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The present feature article describes the different organocatalytic routes for the synthesis of substituted 1,2,3-triazoles. This methodology has recently gained much attention due to its many advantages like high regioselectivity, substrate scope, high yields, and access to novel molecules. The review is divided into 4 different sections based on the active intermediate of the triazole synthesis reactions. The mechanism of each approach is critically discussed and in addition, the advantages and disadvantages of each method are described with relevant examples.

引用

页码：10797 / 10806

页数：10

共 86 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] A strain-promoted [3+2] azide-alkyne cycloaddition for covalent modification of blomolecules in living systems [J].

Agard, NJ ;

Prescher, JA ;

Bertozzi, CR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (46) :15046-15047

[3] An efficient one-pot strategy for the highly regioselective metal-free synthesis of 1,4-disubstituted-1,2,3-triazoles [J].

Ali, Akbar ;

Correa, Arlene G. ;

Alves, Diego ;

Zukerman-Schpector, Julio ;

Westermann, Bernhard ;

Ferreira, Marco A. B. ;

Paixao, Marcio W. .

CHEMICAL COMMUNICATIONS, 2014, 50 (80) :11926-11929

[4] UPSILON-TRIAZOLINES .19. THIOCINO[4,5-D]-1,2,3-TRIAZOLE AND THIOCINO[4,5-D]ISOXAZOLE DERIVATIVES [J].

ALMIRANTE, N ;

FORTI, L .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1984, 21 (04) :1121-1123

[5] 1,2,3-TRIAZOLE-[2',5'-BIS-O-(TERT-BUTYLDIMETHYLSILYL)-BETA-D-RIBOFURANOSYL]-3'-SPIRO-5''-(4''-AMINO-1'',2''-OXATHIOL 2'',2''-DIOXIDE) (TSAO) ANALOGS - SYNTHESIS AND ANTI-HIV-1 ACTIVITY [J].

ALVAREZ, R ;

VELAZQUEZ, S ;

SANFELIX, A ;

AQUARO, S ;

DECLERCQ, E ;

PERNO, CF ;

KARLSSON, A ;

BALZARINI, J ;

CAMARASA, MJ .

JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (24) :4185-4194

[6] 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

[7]

[Anonymous], 2010, Chem. Soc. Rev, V39, P1221

[8] A microwave-assisted click chemistry synthesis of 1,4-disubstituted 1,2,3-triazoles via a copper(I)-catalyzed three-component reaction [J].

Appukkuttan, P ;

Dehaen, W ;

Fokin, VV ;

Van der Eycken, E .

ORGANIC LETTERS, 2004, 6 (23) :4223-4225

[9] Click Dendrimers and Triazole-Related Aspects: Catalysts, Mechanism, Synthesis, and Functions. A Bridge between Dendritic Architectures and Nanomaterials [J].

Astruc, Didier ;

Liang, Liyuan ;

Rapakousiou, Amalia ;

Ruiz, Jaime .

ACCOUNTS OF CHEMICAL RESEARCH, 2012, 45 (04) :630-640

[10] Copper-free click chemistry for dynamic in vivo imaging [J].

Baskin, Jeremy M. ;

Prescher, Jennifer A. ;

Laughlin, Scott T. ;

Agard, Nicholas J. ;

Chang, Pamela V. ;

Miller, Isaac A. ;

Lo, Anderson ;

Codelli, Julian A. ;

Bertozzi, Carolyn R. .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2007, 104 (43) :16793-16797

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