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Synthesis of (E)-2-(1H-tetrazole-5-yl)-3-phenylacrylenenitrile derivatives catalyzed by new ZnO nanoparticles embedded in a thermally stable magnetic periodic mesoporous organosilica under green conditions

ZnO nanoparticles embedded in a magnetic isocyanurate-based periodic mesoporous organosilica (Fe(3)O(4)@PMO–ICS–ZnO) were prepared through a modified environmentally-benign procedure for the first time and properly characterized by appropriate spectroscopic and analytical methods or techniques used...

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Autores principales: Safapoor, Sajedeh, Dekamin, Mohammad G., Akbari, Arezoo, Naimi-Jamal, M. Reza
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9232489/
https://www.ncbi.nlm.nih.gov/pubmed/35750767
http://dx.doi.org/10.1038/s41598-022-13011-9
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author Safapoor, Sajedeh
Dekamin, Mohammad G.
Akbari, Arezoo
Naimi-Jamal, M. Reza
author_facet Safapoor, Sajedeh
Dekamin, Mohammad G.
Akbari, Arezoo
Naimi-Jamal, M. Reza
author_sort Safapoor, Sajedeh
collection PubMed
description ZnO nanoparticles embedded in a magnetic isocyanurate-based periodic mesoporous organosilica (Fe(3)O(4)@PMO–ICS–ZnO) were prepared through a modified environmentally-benign procedure for the first time and properly characterized by appropriate spectroscopic and analytical methods or techniques used for mesoporous materials. The new thermally stable Fe(3)O(4)@PMO–ICS–ZnO nanomaterial with proper active sites and surface area as well as uniform particle size was investigated for the synthesis of medicinally important tetrazole derivatives through cascade condensation and concerted 1,3-cycloaddition reactions as a representative of the Click Chemistry concept. The desired 5-substituted-1H-tetrazole derivatives were smoothly prepared in high to quantitative yields and good purity in EtOH under reflux conditions. Low catalyst loading, short reaction time and the use of green solvents such as EtOH and water instead of carcinogenic DMF as well as easy separation and recyclability of the catalyst for at least five consecutive runs without significant loss of its activity are notable advantages of this new protocol compared to other recent introduced procedures.
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spelling pubmed-92324892022-06-26 Synthesis of (E)-2-(1H-tetrazole-5-yl)-3-phenylacrylenenitrile derivatives catalyzed by new ZnO nanoparticles embedded in a thermally stable magnetic periodic mesoporous organosilica under green conditions Safapoor, Sajedeh Dekamin, Mohammad G. Akbari, Arezoo Naimi-Jamal, M. Reza Sci Rep Article ZnO nanoparticles embedded in a magnetic isocyanurate-based periodic mesoporous organosilica (Fe(3)O(4)@PMO–ICS–ZnO) were prepared through a modified environmentally-benign procedure for the first time and properly characterized by appropriate spectroscopic and analytical methods or techniques used for mesoporous materials. The new thermally stable Fe(3)O(4)@PMO–ICS–ZnO nanomaterial with proper active sites and surface area as well as uniform particle size was investigated for the synthesis of medicinally important tetrazole derivatives through cascade condensation and concerted 1,3-cycloaddition reactions as a representative of the Click Chemistry concept. The desired 5-substituted-1H-tetrazole derivatives were smoothly prepared in high to quantitative yields and good purity in EtOH under reflux conditions. Low catalyst loading, short reaction time and the use of green solvents such as EtOH and water instead of carcinogenic DMF as well as easy separation and recyclability of the catalyst for at least five consecutive runs without significant loss of its activity are notable advantages of this new protocol compared to other recent introduced procedures. Nature Publishing Group UK 2022-06-24 /pmc/articles/PMC9232489/ /pubmed/35750767 http://dx.doi.org/10.1038/s41598-022-13011-9 Text en © The Author(s) 2022 https://creativecommons.org/licenses/by/4.0/Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons licence, and indicate if changes were made. The images or other third party material in this article are included in the article's Creative Commons licence, unless indicated otherwise in a credit line to the material. If material is not included in the article's Creative Commons licence and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this licence, visit http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) .
spellingShingle Article
Safapoor, Sajedeh
Dekamin, Mohammad G.
Akbari, Arezoo
Naimi-Jamal, M. Reza
Synthesis of (E)-2-(1H-tetrazole-5-yl)-3-phenylacrylenenitrile derivatives catalyzed by new ZnO nanoparticles embedded in a thermally stable magnetic periodic mesoporous organosilica under green conditions
title Synthesis of (E)-2-(1H-tetrazole-5-yl)-3-phenylacrylenenitrile derivatives catalyzed by new ZnO nanoparticles embedded in a thermally stable magnetic periodic mesoporous organosilica under green conditions
title_full Synthesis of (E)-2-(1H-tetrazole-5-yl)-3-phenylacrylenenitrile derivatives catalyzed by new ZnO nanoparticles embedded in a thermally stable magnetic periodic mesoporous organosilica under green conditions
title_fullStr Synthesis of (E)-2-(1H-tetrazole-5-yl)-3-phenylacrylenenitrile derivatives catalyzed by new ZnO nanoparticles embedded in a thermally stable magnetic periodic mesoporous organosilica under green conditions
title_full_unstemmed Synthesis of (E)-2-(1H-tetrazole-5-yl)-3-phenylacrylenenitrile derivatives catalyzed by new ZnO nanoparticles embedded in a thermally stable magnetic periodic mesoporous organosilica under green conditions
title_short Synthesis of (E)-2-(1H-tetrazole-5-yl)-3-phenylacrylenenitrile derivatives catalyzed by new ZnO nanoparticles embedded in a thermally stable magnetic periodic mesoporous organosilica under green conditions
title_sort synthesis of (e)-2-(1h-tetrazole-5-yl)-3-phenylacrylenenitrile derivatives catalyzed by new zno nanoparticles embedded in a thermally stable magnetic periodic mesoporous organosilica under green conditions
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9232489/
https://www.ncbi.nlm.nih.gov/pubmed/35750767
http://dx.doi.org/10.1038/s41598-022-13011-9
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