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Biginelli Reaction Catalyzed by Copper Nanoparticles

We recently reported a novel synthesis of copper nanoparticles from copper sulphate utilizing the charge-compensatory effect of ionic liquid [bmim]BF(4) and ethylene glycol. The nanoparticles were characterized and found to be stable for one year. Here we hypothesize that the stabilized nanoparticle...

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Detalles Bibliográficos
Autores principales: Dewan, Manika, Kumar, Ajeet, Saxena, Amit, De, Arnab, Mozumdar, Subho
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Public Library of Science 2012
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3422326/
https://www.ncbi.nlm.nih.gov/pubmed/22912792
http://dx.doi.org/10.1371/journal.pone.0043078
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author Dewan, Manika
Kumar, Ajeet
Saxena, Amit
De, Arnab
Mozumdar, Subho
author_facet Dewan, Manika
Kumar, Ajeet
Saxena, Amit
De, Arnab
Mozumdar, Subho
author_sort Dewan, Manika
collection PubMed
description We recently reported a novel synthesis of copper nanoparticles from copper sulphate utilizing the charge-compensatory effect of ionic liquid [bmim]BF(4) and ethylene glycol. The nanoparticles were characterized and found to be stable for one year. Here we hypothesize that the stabilized nanoparticles should be able to catalyze one-pot multicomponent organic reactions. We show that the nanoparticles catalyzed Biginelli reaction at room temperature to give the product 3,4-dihydopyrimidinone (>90% yield in ∼15 minutes) from aldehydes, β-diketoester (ethylacetoacetate) and urea (or thiourea). ). Remarkably, such high yields and rapid kinetics was found to be independent of the electronic density on the reactant aryl-aldehyde. This was probably because even the surface-active particles reacted faster in the presence of ionic liquid as compared to conventional methods. The heterocyclic dihydropyrimidinones (DHPMs) and their derivatives are widely used in natural and synthetic organic chemistry due to their wide spectrum of biological and therapeutic properties (resulting from their antibacterial, antiviral, antitumor and anti-inflammatory activities. Our method has an easy work-up procedure and the nanoparticles could be recycled with minimal loss of efficiency.
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spelling pubmed-34223262012-08-21 Biginelli Reaction Catalyzed by Copper Nanoparticles Dewan, Manika Kumar, Ajeet Saxena, Amit De, Arnab Mozumdar, Subho PLoS One Research Article We recently reported a novel synthesis of copper nanoparticles from copper sulphate utilizing the charge-compensatory effect of ionic liquid [bmim]BF(4) and ethylene glycol. The nanoparticles were characterized and found to be stable for one year. Here we hypothesize that the stabilized nanoparticles should be able to catalyze one-pot multicomponent organic reactions. We show that the nanoparticles catalyzed Biginelli reaction at room temperature to give the product 3,4-dihydopyrimidinone (>90% yield in ∼15 minutes) from aldehydes, β-diketoester (ethylacetoacetate) and urea (or thiourea). ). Remarkably, such high yields and rapid kinetics was found to be independent of the electronic density on the reactant aryl-aldehyde. This was probably because even the surface-active particles reacted faster in the presence of ionic liquid as compared to conventional methods. The heterocyclic dihydropyrimidinones (DHPMs) and their derivatives are widely used in natural and synthetic organic chemistry due to their wide spectrum of biological and therapeutic properties (resulting from their antibacterial, antiviral, antitumor and anti-inflammatory activities. Our method has an easy work-up procedure and the nanoparticles could be recycled with minimal loss of efficiency. Public Library of Science 2012-08-17 /pmc/articles/PMC3422326/ /pubmed/22912792 http://dx.doi.org/10.1371/journal.pone.0043078 Text en © 2012 Dewan et al http://creativecommons.org/licenses/by/4.0/ This is an open-access article distributed under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are properly credited.
spellingShingle Research Article
Dewan, Manika
Kumar, Ajeet
Saxena, Amit
De, Arnab
Mozumdar, Subho
Biginelli Reaction Catalyzed by Copper Nanoparticles
title Biginelli Reaction Catalyzed by Copper Nanoparticles
title_full Biginelli Reaction Catalyzed by Copper Nanoparticles
title_fullStr Biginelli Reaction Catalyzed by Copper Nanoparticles
title_full_unstemmed Biginelli Reaction Catalyzed by Copper Nanoparticles
title_short Biginelli Reaction Catalyzed by Copper Nanoparticles
title_sort biginelli reaction catalyzed by copper nanoparticles
topic Research Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3422326/
https://www.ncbi.nlm.nih.gov/pubmed/22912792
http://dx.doi.org/10.1371/journal.pone.0043078
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