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Issue 9, 2013
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Synthesis of 3,3-disubstituted oxindoles by one-pot integrated Brønsted base-catalyzed trichloroacetimidation of 3-hydroxyoxindoles and Brønsted acid-catalyzed nucleophilic substitution reaction

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Abstract

Treatment of 3-hydroxyoxindoles with trichloroacetonitrile (1.3 equiv.) and a catalytic amount of DBU (0.1 equiv.) followed by addition of nucleophiles (1.5 equiv.) and diphenylphosphoric acid (0.2 equiv.) afforded the 3,3-disubstituted oxindoles in good to excellent yields. DFT computations supported the notion that the reaction went through the 1-alkyl-2-oxo-2H-indol-1-ium intermediate.

Graphical abstract: Synthesis of 3,3-disubstituted oxindoles by one-pot integrated Brønsted base-catalyzed trichloroacetimidation of 3-hydroxyoxindoles and Brønsted acid-catalyzed nucleophilic substitution reaction

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Publication details

The article was received on 12 Nov 2012, accepted on 02 Jan 2013 and first published on 03 Jan 2013


Article type: Paper
DOI: 10.1039/C2OB27196F
Citation: Org. Biomol. Chem., 2013,11, 1533-1536
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    Synthesis of 3,3-disubstituted oxindoles by one-pot integrated Brønsted base-catalyzed trichloroacetimidation of 3-hydroxyoxindoles and Brønsted acid-catalyzed nucleophilic substitution reaction

    C. Piemontesi, Q. Wang and J. Zhu, Org. Biomol. Chem., 2013, 11, 1533
    DOI: 10.1039/C2OB27196F

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