New Synthons of 3-Hydroxyquinoline Derivatives Through SEAr

Author(s): Mohammed A. M. Massoud, Serry A. El Bialy, Waleed A. Bayoumi, Walaa M. El Husseiny.

Journal Name: Letters in Organic Chemistry

Volume 11 , Issue 9 , 2014

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Graphical Abstract:


A new series of 3-hydroxyquinoline derivatives 2a-c has been synthesized by decarboxylation of corresponding quinoline-4-carboxylic acid derivatives 1a-c. These 3-hydroxyquinolines have been subjected to a number of electrophilic aromatic substitution reactions (SEAr) at C4 to obtain the target structures; 3, 4, 7, 8 and 10 through: bromination, formylation, Mannich reaction, coupling with diazonium salt and acylation, respectively. In addition, formation of fused pyrano[2,3-c]quinolin-3-one 5 and chalcone 11 were done. Trials for formation of chalcone analogue 6 were failed indicating 100% of 3-hydroxy tautomer of 2a-c. All the obtained compounds can act as good chelators and contain at least 3 H-bond acceptor groups. All compounds were evaluated for antioxidant activity by ABTS assay.

Keywords: 3-Hydroxyquinolines, electrophilic aromatic substitution, antioxidant, ABTS assay.

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Article Details

Year: 2014
Page: [693 - 699]
Pages: 7
DOI: 10.2174/157017861109140903105543
Price: $58

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