Sustainable Access to Acridin-9-(10H)ones with an Embedded m-Terphenyl Moiety Based on a Three-Component Reaction

A Ce(IV)-catalyzed three-component reaction between chalcones, anilines and β-ketoesters followed by a microwave-assisted thermal cyclization afforded 1,3-diaryl-1,2-dihydroacridin-9(10H)-ones. Their microwave irradiation in nitrobenzene, acting both as solvent and oxidant, afforded fully unsaturate...

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Autores principales: Rocchi, Damiano, Gómez-Carpintero, Jorge, González, Juan F., Menéndez, Jose Carlos
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2020
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7731126/
https://www.ncbi.nlm.nih.gov/pubmed/33260917
http://dx.doi.org/10.3390/molecules25235565
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author Rocchi, Damiano
Gómez-Carpintero, Jorge
González, Juan F.
Menéndez, Jose Carlos
author_facet Rocchi, Damiano
Gómez-Carpintero, Jorge
González, Juan F.
Menéndez, Jose Carlos
author_sort Rocchi, Damiano
collection PubMed
description A Ce(IV)-catalyzed three-component reaction between chalcones, anilines and β-ketoesters followed by a microwave-assisted thermal cyclization afforded 1,3-diaryl-1,2-dihydroacridin-9(10H)-ones. Their microwave irradiation in nitrobenzene, acting both as solvent and oxidant, afforded fully unsaturated 1,3-diarylacridin-9(10H)-ones, which combine acridin-9-(10H)one and m-terphenyl moieties. Overall, the route generates three C-C and one C-N bond and has the advantage of requiring a single chromatographic separation.
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spelling pubmed-77311262020-12-12 Sustainable Access to Acridin-9-(10H)ones with an Embedded m-Terphenyl Moiety Based on a Three-Component Reaction Rocchi, Damiano Gómez-Carpintero, Jorge González, Juan F. Menéndez, Jose Carlos Molecules Article A Ce(IV)-catalyzed three-component reaction between chalcones, anilines and β-ketoesters followed by a microwave-assisted thermal cyclization afforded 1,3-diaryl-1,2-dihydroacridin-9(10H)-ones. Their microwave irradiation in nitrobenzene, acting both as solvent and oxidant, afforded fully unsaturated 1,3-diarylacridin-9(10H)-ones, which combine acridin-9-(10H)one and m-terphenyl moieties. Overall, the route generates three C-C and one C-N bond and has the advantage of requiring a single chromatographic separation. MDPI 2020-11-27 /pmc/articles/PMC7731126/ /pubmed/33260917 http://dx.doi.org/10.3390/molecules25235565 Text en © 2020 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Rocchi, Damiano
Gómez-Carpintero, Jorge
González, Juan F.
Menéndez, Jose Carlos
Sustainable Access to Acridin-9-(10H)ones with an Embedded m-Terphenyl Moiety Based on a Three-Component Reaction
title Sustainable Access to Acridin-9-(10H)ones with an Embedded m-Terphenyl Moiety Based on a Three-Component Reaction
title_full Sustainable Access to Acridin-9-(10H)ones with an Embedded m-Terphenyl Moiety Based on a Three-Component Reaction
title_fullStr Sustainable Access to Acridin-9-(10H)ones with an Embedded m-Terphenyl Moiety Based on a Three-Component Reaction
title_full_unstemmed Sustainable Access to Acridin-9-(10H)ones with an Embedded m-Terphenyl Moiety Based on a Three-Component Reaction
title_short Sustainable Access to Acridin-9-(10H)ones with an Embedded m-Terphenyl Moiety Based on a Three-Component Reaction
title_sort sustainable access to acridin-9-(10h)ones with an embedded m-terphenyl moiety based on a three-component reaction
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7731126/
https://www.ncbi.nlm.nih.gov/pubmed/33260917
http://dx.doi.org/10.3390/molecules25235565
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