A novel one-pot tandem process involving Knoevenagel condensation, Michael addition, selective amidation, and Paal-Knorr cyclization to diverse functionalized 3-hydroxy-2-furanyl-acrylamides from simple 2-oxoaldehydes and aroylacetonitriles was presented. Attempts were also made to expand the scope of the reaction to different 2-heteroarylfurans. The packing diagram of the molecules viewed down along the α-axis of the unit cell showed a characteristic intramolecular classical O-H···O hydrogen bond between hydroxyl and carbonyl O atoms leading to self-associated (Z)-2-furanyl-acrylamides.