Transformations of 2‐aryl‐4‐(2‐oxopyrrolidinyl‐1)‐1,2,3,4‐tetrahydroquinolines, cycloadducts of the BiCl₃‐catalyzed three‐component Povarov reaction: Oxidation and reduction processes towards new potentially bioactive 2‐arylquinoline derivatives

Abstract

Abstract magnified image Synthesis and spectral characterization of new series of 2‐aryl‐4‐(2‐oxopyrrolidinyl‐1)‐1,2,3,4‐tetrahydroquinolines and their aromatic analogs, 2‐arylquinolines are reported. It was found that substituted tetrahydroquinoline precursors are easily prepared using BiCl 3 ‐catalyzed three‐component Povarov reaction between 4‐nitrobenzaldehyde or 2‐naphtylcarboxyaldehyde, anilines and N ‐vinylpyrrolidin‐2‐one, and could be transformed via oxidation and reduction processes into potentially bioactive 2‐arylquinoline derivatives, unsubstituted at the C‐4 position. The all set of (tetrahydro)quinolines were characterized by IR, 1 H and 13 C‐NMR spectroscopy. J. Heterocyclic Chem., (2010).