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Supramolecular Cu(ii) nanoparticles supported on a functionalized chitosan containing urea and thiourea bridges as a recoverable nanocatalyst for efficient synthesis of 1H-tetrazoles
A cost-effective and convenient method for supporting of Cu(ii) nanoparticles on a modified chitosan backbone containing urea and thiourea bridges using thiosemicarbazide (TS), pyromellitic dianhydride (PMDA) and toluene-2,4-diisocyanate (TDI) linkers was designed. The prepared supramolecular (CS–TD...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2023
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10493853/ https://www.ncbi.nlm.nih.gov/pubmed/37701273 http://dx.doi.org/10.1039/d3ra01989f |
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author | Bondarian, Shirin Dekamin, Mohammad G. Valiey, Ehsan Naimi-Jamal, M. Reza |
author_facet | Bondarian, Shirin Dekamin, Mohammad G. Valiey, Ehsan Naimi-Jamal, M. Reza |
author_sort | Bondarian, Shirin |
collection | PubMed |
description | A cost-effective and convenient method for supporting of Cu(ii) nanoparticles on a modified chitosan backbone containing urea and thiourea bridges using thiosemicarbazide (TS), pyromellitic dianhydride (PMDA) and toluene-2,4-diisocyanate (TDI) linkers was designed. The prepared supramolecular (CS–TDI–PMDA–TS–Cu(ii)) nanocomposite was characterized by using Fourier-transform infrared (FT-IR) spectroscopy, field emission scanning electron microscopy (FESEM), thermogravimetry/differential thermogravimetry analysis (TGA/DTA), energy-dispersive X-ray spectroscopy (EDS), EDS elemental mapping and X-ray diffraction (XRD). The obtained supramolecular CS–TDI–PMDA–TS–Cu(ii) nanomaterial was demonstrated to act as a multifunctional nanocatalyst for promoting of multicomponent cascade Knoevenagel condensation/click 1,3-dipolar azide–nitrile cycloaddition reactions very efficiently between aromatic aldehydes, sodium azide and malononitrile under solvent-free conditions and affording the corresponding (E)-2-(1H-tetrazole-5-yl)-3-arylacrylenenitrile derivatives. Low catalyst loading, working under solvent-free conditions and short reaction time as well as easy preparation and recycling, and reuse of the catalyst for five consecutive cycles without considerable decrease in its catalytic efficiency make it a suitable candidate for the catalytic reactions promoted by Cu species. |
format | Online Article Text |
id | pubmed-10493853 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-104938532023-09-12 Supramolecular Cu(ii) nanoparticles supported on a functionalized chitosan containing urea and thiourea bridges as a recoverable nanocatalyst for efficient synthesis of 1H-tetrazoles Bondarian, Shirin Dekamin, Mohammad G. Valiey, Ehsan Naimi-Jamal, M. Reza RSC Adv Chemistry A cost-effective and convenient method for supporting of Cu(ii) nanoparticles on a modified chitosan backbone containing urea and thiourea bridges using thiosemicarbazide (TS), pyromellitic dianhydride (PMDA) and toluene-2,4-diisocyanate (TDI) linkers was designed. The prepared supramolecular (CS–TDI–PMDA–TS–Cu(ii)) nanocomposite was characterized by using Fourier-transform infrared (FT-IR) spectroscopy, field emission scanning electron microscopy (FESEM), thermogravimetry/differential thermogravimetry analysis (TGA/DTA), energy-dispersive X-ray spectroscopy (EDS), EDS elemental mapping and X-ray diffraction (XRD). The obtained supramolecular CS–TDI–PMDA–TS–Cu(ii) nanomaterial was demonstrated to act as a multifunctional nanocatalyst for promoting of multicomponent cascade Knoevenagel condensation/click 1,3-dipolar azide–nitrile cycloaddition reactions very efficiently between aromatic aldehydes, sodium azide and malononitrile under solvent-free conditions and affording the corresponding (E)-2-(1H-tetrazole-5-yl)-3-arylacrylenenitrile derivatives. Low catalyst loading, working under solvent-free conditions and short reaction time as well as easy preparation and recycling, and reuse of the catalyst for five consecutive cycles without considerable decrease in its catalytic efficiency make it a suitable candidate for the catalytic reactions promoted by Cu species. The Royal Society of Chemistry 2023-09-11 /pmc/articles/PMC10493853/ /pubmed/37701273 http://dx.doi.org/10.1039/d3ra01989f Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/ |
spellingShingle | Chemistry Bondarian, Shirin Dekamin, Mohammad G. Valiey, Ehsan Naimi-Jamal, M. Reza Supramolecular Cu(ii) nanoparticles supported on a functionalized chitosan containing urea and thiourea bridges as a recoverable nanocatalyst for efficient synthesis of 1H-tetrazoles |
title | Supramolecular Cu(ii) nanoparticles supported on a functionalized chitosan containing urea and thiourea bridges as a recoverable nanocatalyst for efficient synthesis of 1H-tetrazoles |
title_full | Supramolecular Cu(ii) nanoparticles supported on a functionalized chitosan containing urea and thiourea bridges as a recoverable nanocatalyst for efficient synthesis of 1H-tetrazoles |
title_fullStr | Supramolecular Cu(ii) nanoparticles supported on a functionalized chitosan containing urea and thiourea bridges as a recoverable nanocatalyst for efficient synthesis of 1H-tetrazoles |
title_full_unstemmed | Supramolecular Cu(ii) nanoparticles supported on a functionalized chitosan containing urea and thiourea bridges as a recoverable nanocatalyst for efficient synthesis of 1H-tetrazoles |
title_short | Supramolecular Cu(ii) nanoparticles supported on a functionalized chitosan containing urea and thiourea bridges as a recoverable nanocatalyst for efficient synthesis of 1H-tetrazoles |
title_sort | supramolecular cu(ii) nanoparticles supported on a functionalized chitosan containing urea and thiourea bridges as a recoverable nanocatalyst for efficient synthesis of 1h-tetrazoles |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10493853/ https://www.ncbi.nlm.nih.gov/pubmed/37701273 http://dx.doi.org/10.1039/d3ra01989f |
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