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 (<i>Z</i>)-2-furanyl-acrylamides

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 (<i>Z</i>)-2-furanyl-acrylamides

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 (<i>Z</i>)-2-furanyl-acrylamides

Amino Catalytic Oxidative Thioesterification Approach to α‑Ketothioesters

An efficient metal-free method for the synthesis of α-ketothioesters is described for the first time. This reaction features the ability of pyrrolidine to fine-tune the reaction between 2-oxoaldehyde and thiols through iminium to the desired product in moderate to good yields. As an advantage, no external oxidants or metal catalysts are required in our method. Reactions performed under modified conditions lead to an apparent balance in reactivity of secondary amine and thiols toward 2-oxoaldehydes

Metal-Free Oxidative Amidation of 2‑Oxoaldehydes: A Facile Access to α‑Ketoamides

A novel and efficient method for the synthesis of α-ketoamides, employing a dimethyl sulfoxide (DMSO)-promoted oxidative amidation reaction between 2-oxoaldehydes and amines under metal-free conditions is presented. Furthermore, mechanistic studies supported an iminium ion-based intermediate as a central feature of reaction wherein C₁-oxygen atom of α-ketoamides is finally derived from DMSO