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Issue 43, 2015
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Highly chemoselective synthesis of dimeric 2-oxindoles with a C-3/C-5′ linkage via Friedel–Crafts alkylations of 2-oxindoles with 3-hydroxy-2-oxindoles

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Abstract

Simple and convenient Lewis acid-catalyzed Friedel–Crafts alkylations of 2-oxindoles as electron rich aromatics with 3-hydroxy-2-oxindoles as electron deficient partners have been developed. The reaction afforded a variety of dimeric 2-oxindoles with a C-3/C-5′ linkage having an all-carbon quaternary center at the pseudobenzylic position in high yields.

Graphical abstract: Highly chemoselective synthesis of dimeric 2-oxindoles with a C-3/C-5′ linkage via Friedel–Crafts alkylations of 2-oxindoles with 3-hydroxy-2-oxindoles

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Publication details

The article was received on 08 Aug 2015, accepted on 24 Aug 2015 and first published on 24 Aug 2015


Article type: Paper
DOI: 10.1039/C5OB01670C
Citation: Org. Biomol. Chem., 2015,13, 10641-10655
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    Highly chemoselective synthesis of dimeric 2-oxindoles with a C-3/C-5′ linkage via Friedel–Crafts alkylations of 2-oxindoles with 3-hydroxy-2-oxindoles

    K. N. Babu, L. K. Kinthada, S. Ghosh and A. Bisai, Org. Biomol. Chem., 2015, 13, 10641
    DOI: 10.1039/C5OB01670C

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