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

✍ Scribed by Vladimir V. Kouznetsov; Carlos M. Meléndez Gómez; John H. Bermúdez Jaimes

• Publisher: Journal of Heterocyclic Chemistry
• Year: 2010
• Tongue: English
• Weight: 132 KB
• Volume: 47
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.441

✦ Synopsis

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).