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Issue 45, 2014
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Lewis acid promoted construction of chromen-4-one and isoflavone scaffolds via regio- and chemoselective domino Friedel–Crafts acylation/Allan–Robinson reaction

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Abstract

A facile and efficient synthesis of chromen-4-one and isoflavone frameworks is achieved by the domino C-acylation/O-acylation/aldolization sequence. This operationally simple one-pot elegant strategy provides structurally unique chromen-4-ones and isoflavones directly from phenols via concomitant formation of multiple C–C and C–O bonds in a single operation. The outcomes of the buttressing effect, substituent dependence, and catalyst and solvent specificity during the course of the Friedel–Crafts acylation reactions are demonstrated and supported by fitting experiments.

Graphical abstract: Lewis acid promoted construction of chromen-4-one and isoflavone scaffolds via regio- and chemoselective domino Friedel–Crafts acylation/Allan–Robinson reaction

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Publication details

The article was received on 14 Aug 2014, accepted on 16 Sep 2014 and first published on 16 Sep 2014


Article type: Paper
DOI: 10.1039/C4OB01743A
Author version available: Download Author version (PDF)
Citation: Org. Biomol. Chem., 2014,12, 9216-9222
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    Lewis acid promoted construction of chromen-4-one and isoflavone scaffolds via regio- and chemoselective domino Friedel–Crafts acylation/Allan–Robinson reaction

    T. Chanda, S. Chowdhury, S. Koley, N. Anand and M. S. Singh, Org. Biomol. Chem., 2014, 12, 9216
    DOI: 10.1039/C4OB01743A

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