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Issue 15, 2014
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Regiodivergent heterocyclization: a strategy for the synthesis of substituted pyrroles and furans using α-formyl ketene dithioacetals as common precursors

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Abstract

The selective construction of a diverse array of five-membered aromatic heterocycles from common starting materials is an attractive and challenging task. We report here that 5-alkylthio-pyrroles, 4-alkylthiocarbonyl-pyrroles and 2-alkylthio-4-tosyl-furans can be prepared, selectively, in a single operation using the readily available α-formyl ketene dithioacetals as common precursors, through their regiodivergent heterocyclization with α-acidic isocyanides controlled by the choice of suitable catalysts/promoters.

Graphical abstract: Regiodivergent heterocyclization: a strategy for the synthesis of substituted pyrroles and furans using α-formyl ketene dithioacetals as common precursors

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Publication details

The article was received on 08 Nov 2013, accepted on 29 Nov 2013 and first published on 02 Dec 2013


Article type: Communication
DOI: 10.1039/C3CC48546C
Citation: Chem. Commun., 2014,50, 1797-1800
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    Regiodivergent heterocyclization: a strategy for the synthesis of substituted pyrroles and furans using α-formyl ketene dithioacetals as common precursors

    T. Wu, L. Pan, X. Xu and Q. Liu, Chem. Commun., 2014, 50, 1797
    DOI: 10.1039/C3CC48546C

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