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Issue 5, 2014
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Zinc-mediated addition of diethyl bromomalonate to alkynes for the cascade reaction towards polysubstituted pyranones and tetracarbonyl derivatives

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Abstract

The zinc-mediated regioselective addition reactions of diethyl bromomalonate and aromatic and aliphatic alkynes were investigated for the synthesis of vinyl malonates. When the vinyl organo-zinc intermediates were reacted with acid chlorides 2H-pyran-2-ones were obtained while the application of oxalyl chloride and an amine led to tetracarbonyl derivatives in a one-pot multi-step reaction sequence.

Graphical abstract: Zinc-mediated addition of diethyl bromomalonate to alkynes for the cascade reaction towards polysubstituted pyranones and tetracarbonyl derivatives

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Publication details

The article was received on 05 Sep 2013, accepted on 02 Nov 2013 and first published on 04 Nov 2013


Article type: Communication
DOI: 10.1039/C3CC46788K
Citation: Chem. Commun., 2014,50, 542-544
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    Zinc-mediated addition of diethyl bromomalonate to alkynes for the cascade reaction towards polysubstituted pyranones and tetracarbonyl derivatives

    A. Miersch, K. Harms and G. Hilt, Chem. Commun., 2014, 50, 542
    DOI: 10.1039/C3CC46788K

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