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Study and application of graphene oxide in the synthesis of 2,3-disubstituted quinolines via a Povarov multicomponent reaction and subsequent oxidation

The carbocatalyzed synthesis of 2,3-disubstituted quinolines is disclosed. This process involved a three-component Povarov reaction of anilines, aldehydes and electron-enriched enol ethers, which gave the substrate for the subsequent oxidation. Graphene oxide (GO) was exploited as a heterogeneous, m...

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Autores principales: Caputo, Samantha, Kovtun, Alessandro, Bruno, Francesco, Ravera, Enrico, Lambruschini, Chiara, Melucci, Manuela, Moni, Lisa
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9135005/
https://www.ncbi.nlm.nih.gov/pubmed/35733657
http://dx.doi.org/10.1039/d2ra01752k
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author Caputo, Samantha
Kovtun, Alessandro
Bruno, Francesco
Ravera, Enrico
Lambruschini, Chiara
Melucci, Manuela
Moni, Lisa
author_facet Caputo, Samantha
Kovtun, Alessandro
Bruno, Francesco
Ravera, Enrico
Lambruschini, Chiara
Melucci, Manuela
Moni, Lisa
author_sort Caputo, Samantha
collection PubMed
description The carbocatalyzed synthesis of 2,3-disubstituted quinolines is disclosed. This process involved a three-component Povarov reaction of anilines, aldehydes and electron-enriched enol ethers, which gave the substrate for the subsequent oxidation. Graphene oxide (GO) was exploited as a heterogeneous, metal-free and sustainable catalyst for both transformations. The multicomponent reaction proceeded under simple and mild reaction conditions, exhibited good functional group tolerance, and could be easily scaled up to the gram level. A selection of tetrahydroquinolines obtained was subsequently aromatized to quinolines. The multistep synthesis could also be performed as a one-pot procedure. Investigation of the real active sites of GO was carried out by performing control experiments and a by full characterization of the carbon material by X-ray photoelectron spectroscopy (XPS) and solid-state nuclear magnetic resonance (ssNMR).
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spelling pubmed-91350052022-06-21 Study and application of graphene oxide in the synthesis of 2,3-disubstituted quinolines via a Povarov multicomponent reaction and subsequent oxidation Caputo, Samantha Kovtun, Alessandro Bruno, Francesco Ravera, Enrico Lambruschini, Chiara Melucci, Manuela Moni, Lisa RSC Adv Chemistry The carbocatalyzed synthesis of 2,3-disubstituted quinolines is disclosed. This process involved a three-component Povarov reaction of anilines, aldehydes and electron-enriched enol ethers, which gave the substrate for the subsequent oxidation. Graphene oxide (GO) was exploited as a heterogeneous, metal-free and sustainable catalyst for both transformations. The multicomponent reaction proceeded under simple and mild reaction conditions, exhibited good functional group tolerance, and could be easily scaled up to the gram level. A selection of tetrahydroquinolines obtained was subsequently aromatized to quinolines. The multistep synthesis could also be performed as a one-pot procedure. Investigation of the real active sites of GO was carried out by performing control experiments and a by full characterization of the carbon material by X-ray photoelectron spectroscopy (XPS) and solid-state nuclear magnetic resonance (ssNMR). The Royal Society of Chemistry 2022-05-26 /pmc/articles/PMC9135005/ /pubmed/35733657 http://dx.doi.org/10.1039/d2ra01752k Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Caputo, Samantha
Kovtun, Alessandro
Bruno, Francesco
Ravera, Enrico
Lambruschini, Chiara
Melucci, Manuela
Moni, Lisa
Study and application of graphene oxide in the synthesis of 2,3-disubstituted quinolines via a Povarov multicomponent reaction and subsequent oxidation
title Study and application of graphene oxide in the synthesis of 2,3-disubstituted quinolines via a Povarov multicomponent reaction and subsequent oxidation
title_full Study and application of graphene oxide in the synthesis of 2,3-disubstituted quinolines via a Povarov multicomponent reaction and subsequent oxidation
title_fullStr Study and application of graphene oxide in the synthesis of 2,3-disubstituted quinolines via a Povarov multicomponent reaction and subsequent oxidation
title_full_unstemmed Study and application of graphene oxide in the synthesis of 2,3-disubstituted quinolines via a Povarov multicomponent reaction and subsequent oxidation
title_short Study and application of graphene oxide in the synthesis of 2,3-disubstituted quinolines via a Povarov multicomponent reaction and subsequent oxidation
title_sort study and application of graphene oxide in the synthesis of 2,3-disubstituted quinolines via a povarov multicomponent reaction and subsequent oxidation
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9135005/
https://www.ncbi.nlm.nih.gov/pubmed/35733657
http://dx.doi.org/10.1039/d2ra01752k
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