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Updated: Jun 23, 2026

Facile Preparation of 4-Substituted Quinazoline Derivatives
Published on: February 15, 2016
Stereoretentive Nucleophilic Aromatic Substitution Accesses Atropisomeric 4-Amino-N-Arylquinolinium Salts
Darren Holmes1, Nia Foster1, Saima Ansari1,2
1School of Chemistry and Chemical Engineering, Queen's University Belfast, Belfast, UK.
Abstract:
We report a novel synthetic route to access N-aryl-4-amino-quinolinium salts via a stereoretentive SNAr-type reaction of amines with atropisomeric N-arylquinolin-4-ones, by in situ formation of the corresponding chloroquinolinium chloride salt. Investigation into the properties of the chiral salts was carried out using x-ray crystallography, DFT analysis, cyclic voltammetry and UV-vis spectroscopy. They were revealed to possess high rotational barriers (with lifetimes of millennia), new photophysical properties and low oxidation potentials. A neutral axially chiral quinolinimine could be obtained by a simple deprotonation of the quinolinium salt.
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