Reaction of β-enaminones and acetylene dicarboxylates: synthesis of substituted 1,2-dihydropyridinones

Abstract

Synthesis of substituted 1,2-dihydropyridinones is described in a one pot reaction of β-enaminones and acetylene dicarboxylates where new C-C and C-N bonds were formed. The title compounds were obtained in moderate to good yields.

DBU‐Promoted Solvent‐Free One‐Pot Multicomponent Synthesis of 2‐Amino‐1,4‐Dihydropyridines From β‐Enaminones, Aromatic Aldehydes and Malononitrile

“…β ‐Enaminones are known to undergo two major types of transformations: the cleavage of C−N bonds or the nucleophilic reaction of the amino group without C−N bond cleavage. Reactions employing β ‐enaminones as C=C−N building blocks without cleavage of C−N bond have been successfully utilized in synthesis of aza‐heterocycles such as pyrroles, [4] imidazoles, [5a] indoles, [5b,6] pyridines, [7a,b] pyrimidines, [7c] dihydropyridines and etc [8]…”

Efficient Synthesis of Bicyclic 2‐Pyridinones and 6‐Amino‐2‐pyridinones by the Regioselective Cycloaddition of Nitro Ketene Aminal with 3‐Hydroxy‐2‐aryl‐acrylate

“…Pyridinones are a unique class of six-membered heterocyclic scaffolds with both a carbonyl group and nitrogen heteroatom. [1] Despite their small size and low molecular mass, they can be employed as bioisosteres for amides, pyridines, pyrazines, and phenol rings. They have also served as a polar replacement for four hydrogen bond acceptors and a hydrogen bond donor.…”

Convenient Synthesis and Biological Activity of 4-minomethylene 1-phenylpyrazolidine-3,5-diones

“…These category of compounds showed significant reactivity in a wide variety of nucleophilic and electrophilic substitution [1,2], photochemical [3], reduction and oxidation reactions [4,5]. Also, they have been employed as synthons of a wide variety of biologically and medicinally active compounds [6,7], as well as of pharmaceutical compounds having anti-epileptic [8], antibacterial [9,10], anti-inflammatory [10], anticonvulsant [11], antitumor [12] and anti-parasitic activities [13]. In addition to this wide spectrum of activity, enaminones revealed good stability under simulated physiological pH conditions and low toxicity [14].…”