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Issue 3, 2012
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Domino reactions in water: diastereoselective synthesis of densely functionalized indolyldihydrofuran derivatives

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Abstract

A library of trans-5-aroyl-2-(indol-3-yl)-4-aryl-4,5-dihydrofuran-3-carbonitriles was diastereoselectively synthesized in excellent yields from the reaction of 2-(3-indolylcarbonyl)-3-aryl-2-propenenitriles with (2-aryl-2-oxoethyl)pyridinium bromides in the presence of triethylamine via a simple, user-friendly domino process carried out in water. Extraction and chromatographic steps were avoided, since the final products could be simply filtered from the aqueous reaction medium and recrystallized. This one-pot transformation generates one C–C and one C–O bond and presumably proceeds by a domino sequence involving the generation of a pyridinium ylide, a Michael addition and a final annulation via intramolecular nucleophilic substitution.

Graphical abstract: Domino reactions in water: diastereoselective synthesis of densely functionalized indolyldihydrofuran derivatives

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Publication details

The article was received on 25 Nov 2011, accepted on 27 Dec 2011 and first published on 23 Jan 2012


Article type: Paper
DOI: 10.1039/C2GC16517A
Citation: Green Chem., 2012,14, 750-757
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    Domino reactions in water: diastereoselective synthesis of densely functionalized indolyldihydrofuran derivatives

    P. Gunasekaran, K. Balamurugan, S. Sivakumar, S. Perumal, J. C. Menéndez and A. I. Almansour, Green Chem., 2012, 14, 750
    DOI: 10.1039/C2GC16517A

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