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Updated: Oct 20, 2025

Facile Preparation of 4-Substituted Quinazoline Derivatives
Published on: February 15, 2016
Catalytic atroposelective dynamic kinetic resolutions and kinetic resolutions towards 3-arylquinolines via SNAr
Mariel M Cardenas1, Mirza A Saputra1, Deane A Gordon1
1College of Sciences, Department of Chemistry and Biochemistry, San Diego State University, 5500 Campanile Drive, San Diego, California, 92182-1030, USA. JGustafson@sdsu.edu.
Abstract:
Herein we report the catalytic atroposelective syntheses of pharmaceutically relevant 3-arylquinolines via the nucleophilic aromatic substitution (SNAr) of thiophenols into 3-aryl-2-fluoroquinolines mediated by catalytic amounts of Cinchona alkaloid-derived ureas. These reactions displayed a spectrum of dynamic kinetic resolution (DKR) and kinetic resolution (KR) characters depending upon the stereochemical stability of the starting material. Low barrier substrates proceeded via DKR while higher barrier substrates proceeded via KR. On the other hand, substrates with intermediate stabilities displayed hallmarks of both DKR and KR. Finally, we also show that we can functionalize the atropisomerically enriched quinolines into pharmaceutically privileged scaffolds with minimal observed racemization.
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