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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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2022-12, Vol.27 (23), p.8545
Main Authors: Tlustý, Martin, Eigner, Václav, Dvořáková, Hana, Lhoták, Pavel
Format: Article
Language:English
Subjects:
Aldehydes
Ammonium
Ammonium compounds
Ammonium paratungstate
Ammonium salts
Aromatic compounds
calixarene
Chromatography
Complexation
Cyclization
Enantiomers
inherent chirality
mercuration
meta-substitution
Miller, Von
Organic compounds
Quaternary Ammonium Compounds - chemistry
Quaternary ammonium salts
quinoline formation
Quinolines
Stoichiometry
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Summary: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 -methylammonium salts was demonstrated.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules27238545