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

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 Ag 2 CO 3 -promoted reaction starting from 3-oxo amides via C-N bond cleavage. A silver/base-promoted regio- or stereoselective synthesis of diverse furan-3-carboxamides and ( Z )-enaminones starting from 3-oxo-amides and propargyl alcohols has been developed.