A Supported Copper Hydroxide on Titanium Oxide as an Efficient Reusable Heterogeneous Catalyst for 1,3-Dipolar Cycloaddition of Organic Azides to Terminal Alkynes

2009 ◽  
Vol 15 (40) ◽  
pp. 10464-10472 ◽  
Author(s):  
Kazuya Yamaguchi ◽  
Takamichi Oishi ◽  
Tatsuyori Katayama ◽  
Noritaka Mizuno
Keyword(s):  
Heterogeneous Catalyst ◽  
Titanium Oxide ◽  
Dipolar Cycloaddition ◽  
Terminal Alkynes ◽  
Copper Hydroxide ◽  
Organic Azides

A metal–organic framework as a highly efficient and reusable catalyst for the solvent-free 1,3-dipolar cycloaddition of organic azides to alkynes

2015 ◽  
Vol 2 (1) ◽  
pp. 42-46 ◽  
Author(s):  
Peng Li ◽  
Sridhar Regati ◽  
Huicai Huang ◽  
Hadi D. Arman ◽  
John C.-G. Zhao ◽  
...  
Keyword(s):  
Metal Organic Framework ◽  
Solvent Free ◽  
Regioselective Synthesis ◽  
Dipolar Cycloaddition ◽  
Reusable Catalyst ◽  
Terminal Alkynes ◽  
Organic Azides ◽  
Highly Efficient ◽  
Solvent Free Conditions ◽  
Metal Organic

A new highly efficient and reusable Cu-MOF has been developed for the regioselective synthesis of 1,2,3-triazoles via the 1,3-dipolar cycloaddition of organic azides to terminal alkynes under solvent-free conditions.

Synthesis of Novel 1,2,3-Triazole Derivatives of Isocoumarins and 3,4-Dihydroisocoumarin with Potential Antiplasmodial Activity In Vitro

2020 ◽  
Vol 16 ◽  
Author(s):  
Lucas da Silva Santos ◽  
Matheus Fillipe Langanke de Carvalho ◽  
Ana Claudia de Souza Pinto ◽  
Amanda Luisa da Fonseca ◽  
Julio César Dias Lopes ◽  
...  
Keyword(s):  
Triazole Ring ◽  
Antiplasmodial Activity ◽  
World Health ◽  
Dipolar Cycloaddition ◽  
Terminal Alkynes ◽  
The World ◽  
Ic50 Values ◽  
Derivatives Of ◽  
Active Substances

Background: Malaria greatly affects the world health, having caused more than 228 million cases only in 2018. The emergence of drug resistance is one of the main problems in its treatment, demonstrating the urge for the development of new antimalarial drugs. Objective: Synthesis and in vitro antiplasmodial evaluation of triazole compounds derived from isocoumarins and a 3,4- dihydroisocoumarin. Method: The compounds were synthesized in 4 to 6-step reactions with the formation of the triazole ring via the Copper(I)-catalyzed 1,3-dipolar cycloaddition between isocoumarin or 3,4-dihydroisocoumarin azides and terminal alkynes. This key reaction provided compounds with an unprecedented connection of isocoumarin or 3,4-dihydroisocoumarin and the 1,2,3-triazole ring. The products were tested for their antiplasmodial activity against a Plasmodium falciparum chloroquine resistant and sensitive strains (W2 and 3D7, respectively). Results: Thirty-one substances were efficiently obtained by the proposed routes with an overall yield of 25-53%. The active substances in the antiplasmodial test displayed IC50 values ranging from 0.68-2.89 μM and 0.85-2.07 μM against W2 and 3D7 strains, respectively.

scholarly journals Green ultrasound-assisted three-component click synthesis of novel 1H-1,2,3-triazole carrying benzothiazoles and fluorinated-1,2,4-triazole conjugates and their antimicrobial evaluation

2017 ◽  
Vol 67 (3) ◽  
pp. 309-324 ◽  
Author(s):  
Nadjet Rezki ◽  
Mohamed Reda Aouad
Keyword(s):  
Antimicrobial Activity ◽  
Cycloaddition Reaction ◽  
Dipolar Cycloaddition ◽  
Terminal Alkynes ◽  
One Pot ◽  
Alkyl Aryl ◽  
Antimicrobial Evaluation ◽  
Ultrasound Assisted ◽  
Click Synthesis

AbstractThe present study describes an efficient and ecofriendly, ultrasound, one-pot click cycloaddition approach for the construction of a novel series of 1,4-disubstituted-1,2,3-triazoles tethered with fluorinated 1,2,4-triazole-benzothiazole molecular conjugates. It involved three-component condensation of the appropriate bromoacetamide benzothiazole, sodium azide and 4-alkyl/aryl-5-(2-fluorophenyl)-3-(prop-2-ynylthio)-1,2,4-triazoles4a-ethrough a Cu(I)-catalyzed 1,3-dipolar cycloaddition reaction. This approach involvesin situgeneration of azidoacetamide benzothiazole, followed by condensation with terminal alkynes in the presence of CuSO4/Na-ascorbate in aqueous DMSO under both conventional and ultrasound conditions. Some of the designed 1,2,3-triazole conjugates6a-owere recognized for their antimicrobial activity against some bacterial and fungal pathogenic strains.

Synthesis of novel 1,2,3-triazole-substituted tomentosins

2019 ◽  
Vol 74 (3) ◽  
pp. 273-281 ◽  
Author(s):  
Mohamed Zaki ◽  
Abdelouahd Oukhrib ◽  
Ahmed El Hakmaoui ◽  
Marie-Aude Hiebel ◽  
Sabine Berteina-Raboin ◽  
...  
Keyword(s):  
Sesquiterpene Lactone ◽  
Column Chromatography ◽  
Michael Addition ◽  
Dipolar Cycloaddition ◽  
Terminal Alkynes

AbstractA series of 1,2,3-triazole-containing tomentosin scaffolds was obtained from tomentosin 1. The synthesis involved a Michael addition of trimethylsilylazide on the α-methylene-γ-lactone function of the natural sesquiterpene lactone 1 to give the diastereoisomers 2 and 3, which were readily separated by column chromatography. These compounds underwent copper-catalyzed Huisgen 1,3-dipolar cycloaddition with various terminal alkynes to provide compounds 4a–h and 5a–h in good yields.

scholarly journals Copper nanoparticles on controlled pore glass (CPG) as highly efficient heterogeneous catalysts for “click reactions”

2020 ◽  
Vol 10 (1) ◽  
Author(s):  
Abdolrahim A. Rafi ◽  
Ismail Ibrahem ◽  
Armando Córdova
Keyword(s):  
Copper Nanoparticles ◽  
Heterogeneous Catalysts ◽  
Catalyst System ◽  
Terminal Alkynes ◽  
Click Reactions ◽  
Dipolar Cycloadditions ◽  
Organic Azides ◽  
Controlled Pore Glass ◽  
Pore Glass ◽  
High Yields

AbstractWe herein report that supported copper nanoparticles (CuNPs) on commercially available controlled pore glass (CPG), which exhibit high mechanical, thermal and chemical stability as compared to other silica-based materials, serve as a useful heterogeneous catalyst system for 1,3-dipolar cycloadditions (“click” reactions) between terminal alkynes and organic azides under green chemistry conditions. The supported CuNPs-CPG catalyst exhibited a broad substrate scope and gave the corresponding triazole products in high yields. The CuNPs-CPG catalyst exhibit recyclability and could be reuced multiple times without contaminating the products with Cu.

1,3-Dipolar Cycloaddition of Organic Azides to Alkynes by a Dicopper-Substituted Silicotungstate

2008 ◽  
Vol 130 (46) ◽  
pp. 15304-15310 ◽  
Author(s):  
Keigo Kamata ◽  
Yoshinao Nakagawa ◽  
Kazuya Yamaguchi ◽  
Noritaka Mizuno
Keyword(s):  
Dipolar Cycloaddition ◽  
Organic Azides
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