Facile Installation of β-Hydroxyarylethylamino Motifs at the C2-Position of Quinoline Moiety via Copper-Catalyzed [3+3]-Cycloaddition Reaction of N-Oxide with N-Ts Aziridine

Abstract

A general and atom-efficient synthesis of quinoline-C2-substituted β-hydroxyarylethylamino derivatives was achieved by copper-catalyzed [3+3]-cycloaddition reaction of N-oxide with N-Ts aziridines. Notably, temperature has a huge impact on this transformation as evidenced by the fact that, at 80 °C, exclusively [3+3]-cycloadduct was isolated whereas, at elevated temperature (140 °C), it has been converted into the aminated product with good yield. Notably, there is no by-product in the overall process. The use of base-free conditions, excellent site-selectivity, and good functional group tolerance are the important features of the process.