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Mesoporous Copper–Magnesium Oxide Hybrid Nanocatalyzed Synthesis of 3-Substituted Isocoumarins from 2-Iodobenzoic Acid and Terminal Alkyne under Green Conditions

[Image: see text] A 3-substituted isocoumarin scaffold has captivated extensive interest in synthetic and medicinal chemistry due to its presence in various natural products with diverse biological activities. Herein, we report a mesoporous CuO@MgO nanocomposite that was prepared via the sugar-blowi...

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Autores principales: Rawat, Manish, Rawat, Diwan S.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10173437/
https://www.ncbi.nlm.nih.gov/pubmed/37179619
http://dx.doi.org/10.1021/acsomega.3c00710
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author Rawat, Manish
Rawat, Diwan S.
author_facet Rawat, Manish
Rawat, Diwan S.
author_sort Rawat, Manish
collection PubMed
description [Image: see text] A 3-substituted isocoumarin scaffold has captivated extensive interest in synthetic and medicinal chemistry due to its presence in various natural products with diverse biological activities. Herein, we report a mesoporous CuO@MgO nanocomposite that was prepared via the sugar-blowing induced confined method with an E-factor of 12.2 and its catalytic potential in the facile synthesis of 3-substituted isocoumarin from 2-iodobenzoic acids and terminal alkynes. Powder X-ray diffraction, scanning electron microscopy, high-resolution transmission electron microscopy, energy-dispersive X-ray analysis, X-ray photoelectron spectroscopy, and Brunauer–Emmett–Teller techniques were utilized for the characterization of the as-prepared nanocomposite. A broad substrate scope, mild reaction conditions, excellent yield in short reaction time, no usage of additives, and better green chemistry metrices such as a low E-factor (0.71), high reaction mass efficiency (58.28%), low process mass efficiency (1.71), and high turnover number (629) are the various advantages of the present synthetic route. The nanocatalyst was recycled and reused up to five runs without significant loss in its catalytic activity and a very low leaching of copper (3.20 ppm) and magnesium ions (0.72 ppm). Powder X-ray diffraction and high-resolution transmission electron microscopy techniques confirmed the structural integrity of the recycled CuO@MgO nanocomposite.
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spelling pubmed-101734372023-05-12 Mesoporous Copper–Magnesium Oxide Hybrid Nanocatalyzed Synthesis of 3-Substituted Isocoumarins from 2-Iodobenzoic Acid and Terminal Alkyne under Green Conditions Rawat, Manish Rawat, Diwan S. ACS Omega [Image: see text] A 3-substituted isocoumarin scaffold has captivated extensive interest in synthetic and medicinal chemistry due to its presence in various natural products with diverse biological activities. Herein, we report a mesoporous CuO@MgO nanocomposite that was prepared via the sugar-blowing induced confined method with an E-factor of 12.2 and its catalytic potential in the facile synthesis of 3-substituted isocoumarin from 2-iodobenzoic acids and terminal alkynes. Powder X-ray diffraction, scanning electron microscopy, high-resolution transmission electron microscopy, energy-dispersive X-ray analysis, X-ray photoelectron spectroscopy, and Brunauer–Emmett–Teller techniques were utilized for the characterization of the as-prepared nanocomposite. A broad substrate scope, mild reaction conditions, excellent yield in short reaction time, no usage of additives, and better green chemistry metrices such as a low E-factor (0.71), high reaction mass efficiency (58.28%), low process mass efficiency (1.71), and high turnover number (629) are the various advantages of the present synthetic route. The nanocatalyst was recycled and reused up to five runs without significant loss in its catalytic activity and a very low leaching of copper (3.20 ppm) and magnesium ions (0.72 ppm). Powder X-ray diffraction and high-resolution transmission electron microscopy techniques confirmed the structural integrity of the recycled CuO@MgO nanocomposite. American Chemical Society 2023-04-24 /pmc/articles/PMC10173437/ /pubmed/37179619 http://dx.doi.org/10.1021/acsomega.3c00710 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Rawat, Manish
Rawat, Diwan S.
Mesoporous Copper–Magnesium Oxide Hybrid Nanocatalyzed Synthesis of 3-Substituted Isocoumarins from 2-Iodobenzoic Acid and Terminal Alkyne under Green Conditions
title Mesoporous Copper–Magnesium Oxide Hybrid Nanocatalyzed Synthesis of 3-Substituted Isocoumarins from 2-Iodobenzoic Acid and Terminal Alkyne under Green Conditions
title_full Mesoporous Copper–Magnesium Oxide Hybrid Nanocatalyzed Synthesis of 3-Substituted Isocoumarins from 2-Iodobenzoic Acid and Terminal Alkyne under Green Conditions
title_fullStr Mesoporous Copper–Magnesium Oxide Hybrid Nanocatalyzed Synthesis of 3-Substituted Isocoumarins from 2-Iodobenzoic Acid and Terminal Alkyne under Green Conditions
title_full_unstemmed Mesoporous Copper–Magnesium Oxide Hybrid Nanocatalyzed Synthesis of 3-Substituted Isocoumarins from 2-Iodobenzoic Acid and Terminal Alkyne under Green Conditions
title_short Mesoporous Copper–Magnesium Oxide Hybrid Nanocatalyzed Synthesis of 3-Substituted Isocoumarins from 2-Iodobenzoic Acid and Terminal Alkyne under Green Conditions
title_sort mesoporous copper–magnesium oxide hybrid nanocatalyzed synthesis of 3-substituted isocoumarins from 2-iodobenzoic acid and terminal alkyne under green conditions
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10173437/
https://www.ncbi.nlm.nih.gov/pubmed/37179619
http://dx.doi.org/10.1021/acsomega.3c00710
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