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.