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Transformations of 2‐aryl‐4‐(2‐oxopyrrolidinyl‐1)‐1,2,3,4‐tetrahydroquinolines, cycloadducts of the BiCl 3 ‐catalyzed three‐component Povarov reaction: Oxidation and reduction processes towards new potentially bioactive 2‐arylquinoline derivatives
Author(s) -
Kouznetsov Vladimir V.,
Meléndez Gómez Carlos M.,
Bermúdez Jaimes John H.
Publication year - 2010
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.441
Subject(s) - chemistry , catalysis , aryl , redox , component (thermodynamics) , nuclear magnetic resonance spectroscopy , combinatorial chemistry , medicinal chemistry , organic chemistry , alkyl , physics , thermodynamics
AbstractSynthesis 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).