Stereoretentive Nucleophilic Aromatic Substitution Accesses Atropisomeric 4-Amino-N-Arylquinolinium Salts.

ABSTRACT: We report a novel synthetic route to access N-aryl-4-amino-quinolinium salts via a stereoretentive S_NAr-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.

SUBMITTER: Holmes D 

PROVIDER: S-EPMC13628526 | biostudies-literature | 2026 Oct

REPOSITORIES: biostudies-literature