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Behavior of 3(2‐pyridinylmethylene)‐5‐aryl‐2(3 H )‐furanones and 3(3‐pyridinylmethylene)‐5‐aryl‐2(3 H )‐furanones as alkylating agents: A comparative study
Author(s) -
Abou Elmagd Wael S. I.
Publication year - 2011
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.709
Subject(s) - chemistry , pyridine , quinoline , aryl , alkylation , aluminium chloride , medicinal chemistry , benzene , diene , solvent , intramolecular force , anhydrous , organic chemistry , alkyl , aluminium , catalysis , natural rubber
3(2‐pyridinylmethylene)‐5‐aryl‐2(3 H )‐furanones and 3(3‐pyridinylmethylene)‐5‐aryl‐2(3 H )‐furanones were prepared as a mixture of (E) and (Z) stereoisomers by condensing pyridine‐2‐carboxaldehyde and pyridine‐3‐carboxaldehyde with 3‐aroylpropionic acids. The reaction of the furanones 6 and 7 with anhydrous aluminium chloride in benzene led to the formation of 4,4‐diaryl‐1‐(2‐pyridinyl)but‐1,3‐diene ( 8 ) and 4,4‐diaryl‐1‐(3‐pyridinyl)but‐1,3‐diene ( 9 ) as mixtures of geometrical (E,E‐ and E,Z‐) stereoisomers via an intermolecular alkylation mode. When the reaction was carried out in tetrachloroethane as a solvent, the reaction of 6 gave 5‐arylquinoline‐7‐carboxylic acid via intramolecular alkylation mode. This may be considered as a novel method for the synthesis of quinoline derivatives. J. Heterocyclic Chem., (2011).