One-Pot Tandem Approach to Functionalized 3‑Hydroxy-2-furanyl-acrylamides

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.