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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...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Nature Publishing Group UK
2022
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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. |
format | Online Article Text |
id | pubmed-9232489 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | Nature Publishing Group UK |
record_format | MEDLINE/PubMed |
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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