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Issue 9, 2013
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Synthesis of 2,4-unsubstituted quinoline-3-carboxylic acid ethyl esters from arylmethyl azides via a domino process

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Abstract

A convenient synthesis of 2,4-unsubstituted quinoline-3-carboxylic acid ethyl esters via a domino process is described. The synthesis employs arylmethyl azides as the precursor which undergoes an acid-promoted rearrangement to give an N-aryl iminium ion. Following the addition with ethyl 3-ethoxyacrylate, intramolecular electrophilic aromatic substitution, elimination and subsequent oxidation, the quinoline products were obtained in moderate to excellent yields.

Graphical abstract: Synthesis of 2,4-unsubstituted quinoline-3-carboxylic acid ethyl esters from arylmethyl azides via a domino process

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Publication details

The article was received on 23 Dec 2012, accepted on 16 Jan 2013 and first published on 18 Jan 2013


Article type: Communication
DOI: 10.1039/C3OB27493D
Citation: Org. Biomol. Chem., 2013,11, 1463-1467

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    Synthesis of 2,4-unsubstituted quinoline-3-carboxylic acid ethyl esters from arylmethyl azides via a domino process

    J. Tummatorn, C. Thongsornkleeb, S. Ruchirawat and T. Gettongsong, Org. Biomol. Chem., 2013, 11, 1463
    DOI: 10.1039/C3OB27493D

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