The present research describes the synthesis of novel 5-benzoyl-N-substituted-amino- and 5-benzoyl-N-sulfonylamino-4-alkylsulfanyl-2-pyridones 5a-c and 6a-c via the reaction of 2-benzoyl-3,3-bis(alkylthio)acrylonitriles 2a-c with N-cyanoacetohydrazide 3 and cyanoaceto-N-phenylsulfonylhydrazide 4, respectively. Also, the reactivity of the compounds 5a-c toward hydrazine hydrate to give product 1...

A new method for the synthesis of β-iodo N-alkenyl 2-pyridones from substituted 2-propargyloxypyridines has been discovered . These compounds present a unique complement of orthogonal functionality and structural characteristics that are unavailable via other routes. The ready access to these compounds renders them an important entry point for the preparation of more complex N-alkyl pyridone-co...

Abstract α-Pyridones and α-pyrones are ubiquitous structural motifs found in natural products biologically active small molecules. Here, we report an Rh-catalyzed electrochemical vinylic C–H annulation of acrylamides with alkynes, affording cyclic good to excellent yield. Divergent syntheses α-pyridones imidates accomplished by employing N- phenyl tosyl as substrates, respectively. Additionally...

The in vivo conversion ratio of N1-methylnicotinamide (NMN) to N1-methyl-2-pyridone-5-carboxamide (2-PY) and N1-methyl-4-pyridone-3-carboxamide (4-PY) as a parameter for the estimation of aldehyde oxidase level in rats was examined. NMN and its pyridones (2-PY and 4-PY) are usually detected in the urine of rats. When we measured the ratio of the amount of pyridones to the total amount of NMN an...

A new LiI-promoted O- to N-alkyl migration has been developed for the conversion of O-alkylated 2-hydroxy pyridines, quinolines, and pyrimidines to the corresponding N-alkylated heterocycles in good to excellent yields (57-99%). This method serves as an efficient means for the preparation of N-benzyl pyridones, quinolones, and pyrimidones.

The 1,6-annulated 2-pyridone motif is found in many biologically active compounds and its close relation to the indolizidine and quinolizidine alkaloid core makes it an attractive building block. A nickel-catalyzed C-H functionalization of 2-pyridones and subsequent cyclization affords 1,6-annulated 2-pyridones by selective intramolecular olefin hydroarylation. The switch between the exo- and e...

In the course of experiments designed to elucidate the structure of reduced diphosphopyridine nucleotide (DPNH) (12), it became necessary to prepare the 2and 6-pyridones of iV-methylnicotinamidel by oxidation of the latter. Huff (5) has described the preparation of N’-methyl-6-pyridone-3-carboxylic acid by alkaline ferricyanide oxidation of either trigonelline or N’-methylnicotinamide. The acid...

An efficient and inexpensive LiI-promoted O- to N-alkyl migration of 2-benzyloxy-, 2-allyloxy-, and 2-propargyloxypyridines and heterocycles is reported. The reaction produces the corresponding N-alkyl 2-pyridones and analogues under green, solvent-free conditions in good to excellent yields (30 examples, 20-97% yield). This method has been shown to be intermolecular and requires heat and lithi...

The transcriptional activator PrfA, a member of the Crp/Fnr family, controls the expression of some key virulence factors necessary for infection by the human bacterial pathogen Listeria monocytogenes. Phenotypic screening identified ring-fused 2-pyridone molecules that at low micromolar concentrations attenuate L. monocytogenes cellular uptake by reducing the expression of virulence genes. The...

The Sandmeyer reaction of differently C-2 substituted N-(prop-2-yn-1-ylamino)pyridines is an efficient, mild, new and practical method for the stereospecific synthesis of (E)-exo-halomethylene bicyclic pyridones bearing the imidazo[1,2-a]pyridine heterocyclic ring system.