Multicomponent Click Synthesis of Potentially Biologically Active Triazoles Catalysed by Copper Nanoparticles on Activated Carbon in Water

Alonso, Francisco; Moglie, Yanina; Radivoy, Gabriel; Yus, Miguel

doi:10.3987/com-11-s(p)81

Cited by 51 publications

(7 citation statements)

References 44 publications

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“…They are also exhibit wide range of biological properties such as anti HIV, antialergic, antimicrobial, antifungal and antitumor. [1][2][3][4][5] In recent years, several different methods have been reported for the synthesis of 1,2,3-triazole derivatives and as a result, the multiple derivatives of triazole ring were synthesized. [6][7][8][9][10][11][12][13][14][15] For the 1,2,3 isomer, copper(I)-catalyzed 1,3-dipolar cycloaddition of substituted azides and terminal alkynes, [3+2] Huisgenʼs cycloaddition reaction, is the most common method for the synthesis of these compounds.…”

Section: Introductionmentioning

confidence: 99%

Ultrasound assisted synthesis of thiazolidine thiones containing 1,2,3-triazoles using Cu/TiO2

Alyari¹,

Mehrabani²,

Allahvirdinesbat³

et al. 2017

Arkivoc

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Oxidised copper nanoparticles on TiO2 have been found to effectively catalyze the multicomponent synthesis of 1,4-disubstituted 1,2,3-triazoles in water under both conventional heating and ultrasonic irradiation conditions. The Cu/TiO2 nanocatalyst is easy to prepare, very versatile and recyclable. Following the optimized conditions, an array of 1,2,3-triazoles containing thiazolidine-2-thiones were synthesized from 5iodomethylthiazolidine-2-thiones, sodium azide, and phenylacetylene. All the compounds were evaluated for antibacterial activitiy and some of them displayed varying levels of antibacterial activity against Staphylococcus aureus and Escherichia coli.

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Section: Introductionmentioning

confidence: 99%

Ultrasound assisted synthesis of thiazolidine thiones containing 1,2,3-triazoles using Cu/TiO2

Alyari¹,

Mehrabani²,

Allahvirdinesbat³

et al. 2017

Arkivoc

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“…Although, there are several reports on CuAAC reactions catalyzed by CuNPs and most of them require high temperature (60‐80 °C) and longer time (2‐24 h),, reactions using our method require ambient temperature and shorter reaction time (30 min–2 h) to furnish the triazoles in water.…”

Section: Resultsmentioning

confidence: 97%

“…Recently, Alonso et al . demonstrated that CuNPs accelerate the one‐pot click reaction involving the ring opening of an epoxide with azides followed by its cycloaddition with alkyne …”

Section: Introductionmentioning

confidence: 99%

In Situ Generation of Copper Nanoparticles by Rongalite and Their Use as Catalyst for Click Chemistry in Water

et al. 2018

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A novel, efficient and green protocol for the copper‐catalyzed azide–alkyne cycloaddition (CuAAC) reaction by using copper nanoparticles (CuNPs), generated in situ by a green reducing agent, rongalite, is reported. Terminal alkynes reacted with benzyl, aryl and alkyl azides in the presence of copper nanoparticles and β ‐cyclodextrin (β‐CD) in water. The reactions exclusively generated the corresponding regiospecific 1,4‐disubstituted 1,2,3‐triazoles in good to excellent yields. Notably, in situ generation of copper nanoparticles does not require any additional stabilizing agents or special reaction conditions. β‐cyclodextrin plays dual role as a stabilizing agent as well as phase transfer catalyst. This protocol is also applicable for gram scale reactions.

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“…. Simultaneously, Alonso and coworkers expanded the scope of Cu‐NPs/C catalyst by producing a variety of potentially biologically active 1,2,3‐triazoles, derived from natural product such as (–)‐menthol, lactic acid, D‐glucose, oestrone, cholesterol and phenacetin …”

Section: Multicomponent Synthesis Using Copper–based Nanocatalystsmentioning

confidence: 99%

Multicomponent Reactions in Organic Synthesis Using Copper‐Based Nanocatalysts

Das

2016

ChemistrySelect

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Environment‐friendly and comparatively inexpensive copper‐based nanoparticles have been extensively explored as highly selective catalysts in C−C and C‐heteroatom bond forming reactions. Among them, multicomponent reactions (MCRs), performed with heterogeneous copper‐based nanocatalysts have undergone an explosive growth in recent years. The one pot character of MCRs delivers smaller amount by‐products compared to classical stepwise synthetic routes, with lower costs, time and energy. These advantages of MCRs, along with a variety of readily available cheap copper‐based nanoparticles, enhance the scope to generate many catalytic systems. The present review primarily aims to illustrate the progress of ex situ or in situ generated copper‐based nanoparticles catalyzed various MCRs towards the synthesis of important organic compounds. The mechanistic aspects of the reactions have been highlighted as well.

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Multicomponent Click Synthesis of Potentially Biologically Active Triazoles Catalysed by Copper Nanoparticles on Activated Carbon in Water

Cited by 51 publications

References 44 publications

Ultrasound assisted synthesis of thiazolidine thiones containing 1,2,3-triazoles using Cu/TiO2

Ultrasound assisted synthesis of thiazolidine thiones containing 1,2,3-triazoles using Cu/TiO2

In Situ Generation of Copper Nanoparticles by Rongalite and Their Use as Catalyst for Click Chemistry in Water

Multicomponent Reactions in Organic Synthesis Using Copper‐Based Nanocatalysts

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