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Issue 41, 2014
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Friedel–Crafts alkylations of electron-rich aromatics with 3-hydroxy-2-oxindoles: scope and limitations

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Abstract

A Lewis acid-catalyzed nucleophilic addition of electron rich aromatics with 3-hydroxy-2-oxindoles 5 was developed. The reaction is believed to proceed through the 2H-indol-2-one ring system 9, which eventually reacts with various electron-rich aromatics to afford a variety of 2-oxindoles with an all-carbon quaternary center at the pseudobenzylic position (4, 8, 13, and 16) in high yields. The methodology provides an expeditious route to the tetracyclic core (3) of diazonamide (1), and azonazine (2) as well as the tricyclic core of asperazine (6a), idiospermuline (6b), and calycosidine (6c) viz. C(3a)-arylpyrroloindolines 7 having an all-carbon quaternary center on further synthetic elaboration.

Graphical abstract: Friedel–Crafts alkylations of electron-rich aromatics with 3-hydroxy-2-oxindoles: scope and limitations

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Publication details

The article was received on 17 Jun 2014, accepted on 07 Aug 2014 and first published on 08 Aug 2014


Article type: Paper
DOI: 10.1039/C4OB01264J
Citation: Org. Biomol. Chem., 2014,12, 8152-8173
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    Friedel–Crafts alkylations of electron-rich aromatics with 3-hydroxy-2-oxindoles: scope and limitations

    L. K. Kinthada, S. Ghosh, K. N. Babu, Mohd. Sharique, S. Biswas and A. Bisai, Org. Biomol. Chem., 2014, 12, 8152
    DOI: 10.1039/C4OB01264J

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