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Issue 40, 2013
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Acid-catalyzed reactions of 3-hydroxy-2-oxindoles with electron-rich substrates: synthesis of 2-oxindoles with all-carbon quaternary center

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Abstract

A Lewis acid catalyzed reaction of in situ generated 2H-indol-2-one (9) with various 2π and other electron-rich substrates has been developed. A variety of electron-rich substrates such as allyl/methallyltrimethylsilane, phenylacetylene, styrenes, acetophenone, and indoles have been used. The methodology provides a straightforward approach for the synthesis of 2-oxindoles with an all-carbon quaternary center at the pseudobenzylic position.

Graphical abstract: Acid-catalyzed reactions of 3-hydroxy-2-oxindoles with electron-rich substrates: synthesis of 2-oxindoles with all-carbon quaternary center

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Publication details

The article was received on 18 Jul 2013, accepted on 21 Aug 2013 and first published on 21 Aug 2013


Article type: Paper
DOI: 10.1039/C3OB41482E
Citation: Org. Biomol. Chem., 2013,11, 6984-6993
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    Acid-catalyzed reactions of 3-hydroxy-2-oxindoles with electron-rich substrates: synthesis of 2-oxindoles with all-carbon quaternary center

    L. K. Kinthada, S. Ghosh, S. De, S. Bhunia, D. Dey and A. Bisai, Org. Biomol. Chem., 2013, 11, 6984
    DOI: 10.1039/C3OB41482E

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