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The Formation of Inherently Chiral Calix[4]quinolines by Doebner–Miller Reaction of Aldehydes and Aminocalixarenes

The formation of inherently chiral calix[4]arenes by the intramolecular cyclization approach suffers from a limited number of suitable substrates for these reactions. Here, we report an easy way to prepare one class of such compounds: calixquinolines, which can be obtained by the reaction of aldehyd...

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Autores principales: Tlustý, Martin, Eigner, Václav, Dvořáková, Hana, Lhoták, Pavel
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9736694/
https://www.ncbi.nlm.nih.gov/pubmed/36500638
http://dx.doi.org/10.3390/molecules27238545
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author Tlustý, Martin
Eigner, Václav
Dvořáková, Hana
Lhoták, Pavel
author_facet Tlustý, Martin
Eigner, Václav
Dvořáková, Hana
Lhoták, Pavel
author_sort Tlustý, Martin
collection PubMed
description The formation of inherently chiral calix[4]arenes by the intramolecular cyclization approach suffers from a limited number of suitable substrates for these reactions. Here, we report an easy way to prepare one class of such compounds: calixquinolines, which can be obtained by the reaction of aldehydes with easily accessible aminocalix[4]arenes in acidic conditions (Doebner–Miller reaction). The synthetic procedure represents a very straightforward approach to the inherently chiral macrocyclic systems. The complexation studies revealed the ability of these compounds to complex quaternary ammonium salts with different stoichiometries depending on the guest molecules. At the same time, the ability of enantioselective complexation of chiral N-methylammonium salts was demonstrated.
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spelling pubmed-97366942022-12-11 The Formation of Inherently Chiral Calix[4]quinolines by Doebner–Miller Reaction of Aldehydes and Aminocalixarenes Tlustý, Martin Eigner, Václav Dvořáková, Hana Lhoták, Pavel Molecules Article The formation of inherently chiral calix[4]arenes by the intramolecular cyclization approach suffers from a limited number of suitable substrates for these reactions. Here, we report an easy way to prepare one class of such compounds: calixquinolines, which can be obtained by the reaction of aldehydes with easily accessible aminocalix[4]arenes in acidic conditions (Doebner–Miller reaction). The synthetic procedure represents a very straightforward approach to the inherently chiral macrocyclic systems. The complexation studies revealed the ability of these compounds to complex quaternary ammonium salts with different stoichiometries depending on the guest molecules. At the same time, the ability of enantioselective complexation of chiral N-methylammonium salts was demonstrated. MDPI 2022-12-04 /pmc/articles/PMC9736694/ /pubmed/36500638 http://dx.doi.org/10.3390/molecules27238545 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/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 (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Tlustý, Martin
Eigner, Václav
Dvořáková, Hana
Lhoták, Pavel
The Formation of Inherently Chiral Calix[4]quinolines by Doebner–Miller Reaction of Aldehydes and Aminocalixarenes
title The Formation of Inherently Chiral Calix[4]quinolines by Doebner–Miller Reaction of Aldehydes and Aminocalixarenes
title_full The Formation of Inherently Chiral Calix[4]quinolines by Doebner–Miller Reaction of Aldehydes and Aminocalixarenes
title_fullStr The Formation of Inherently Chiral Calix[4]quinolines by Doebner–Miller Reaction of Aldehydes and Aminocalixarenes
title_full_unstemmed The Formation of Inherently Chiral Calix[4]quinolines by Doebner–Miller Reaction of Aldehydes and Aminocalixarenes
title_short The Formation of Inherently Chiral Calix[4]quinolines by Doebner–Miller Reaction of Aldehydes and Aminocalixarenes
title_sort formation of inherently chiral calix[4]quinolines by doebner–miller reaction of aldehydes and aminocalixarenes
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9736694/
https://www.ncbi.nlm.nih.gov/pubmed/36500638
http://dx.doi.org/10.3390/molecules27238545
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