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Issue 36, 2018
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Silver(I)/base-promoted propargyl alcohol-controlled regio- or stereoselective synthesis of furan-3-carboxamides and (Z)-enaminones

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Abstract

A novel and facile regioselective synthesis of furan-3-carboxamides by a silver(I)/base-promoted reaction of propargyl alcohol with 3-oxo amides has been demonstrated. This one-pot protocol provides a rapid synthetic approach to diverse trisubstituted furan-3-carboxamides via cascade nucleophilic addition, intramolecular cyclization, elimination, and isomerization reactions. Employing a substituted propargyl alcohol, (Z)-enaminones have been obtained with high stereoselectivities by a Ag2CO3-promoted reaction starting from 3-oxo amides via C–N bond cleavage.

Graphical abstract: Silver(i)/base-promoted propargyl alcohol-controlled regio- or stereoselective synthesis of furan-3-carboxamides and (Z)-enaminones

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Publication details

The article was received on 25 Jul 2018, accepted on 31 Aug 2018 and first published on 06 Sep 2018


Article type: Paper
DOI: 10.1039/C8OB01791C
Citation: Org. Biomol. Chem., 2018,16, 6749-6759
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    Silver(I)/base-promoted propargyl alcohol-controlled regio- or stereoselective synthesis of furan-3-carboxamides and (Z)-enaminones

    S. Sultana, J. Shim, S. H. Kim and Y. R. Lee, Org. Biomol. Chem., 2018, 16, 6749
    DOI: 10.1039/C8OB01791C

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