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Synfacts 2019; 15(12): 1416
DOI: 10.1055/s-0039-1690280
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

1,3-Bis(carboxymethyl)imidazolium Chloride-Catalyzed Synthesis of Quinolines

Contributor(s):
Yasuhiro Uozumi
,
Aya Tazawa
Gisbert P, Albert-Soriano M, Pastor IM. * University of Alicante, Spain
Effective and Sustainable Access to Quinolines and Acridines: A Heterogeneous Imidazolium Salt Mediates C–C and C–N Bond Formation.

Eur. J. Org. Chem. 2019; 4928-4940
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Further Information

Publication History

Publication Date:
18 November 2019 (online)

 
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Key words

quinolines - ionic organic solids - imidazolium organocatalysis

Significance

1,3-Bis(carboxymethyl)imidazolium chloride (bcmim-Cl) catalyzed the reaction of 2-aminobenzaldehydes or 2-aminoacetophenones with ketones under solvent-free conditions to afford the corresponding quinolines in up to 96% yield (eq. 1). Bcmim-Cl also promoted the reaction of 3-acetylquinoline with benzaldehydes (eq. 2) and the tandem reaction of 2-aminobenzophenone, pentane-2,4-dione, and benzaldehydes to afford the corresponding quinolyl chalcones (eq. 3).


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Comment

In the reaction of 2-aminoacetophenone with pentane-2,4-dione, bcmim-Cl was recovered by centrifugation and reused seven times without significant loss of its catalytic activity. The catalytic activity of bcmim-Cl was superior to that of other imidazolium and ammonium salts (eq. 4)


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