A convenient route to pyridones, pyrazolo[2,3‐a]pyrimidines and pyrazolo[5,1‐c]triazines incorporating antipyrine moiety

Abstract

Condensation of 4-aminoantipyrine with ethyl acetoacetate, ethyl benzoylacetate, and ethyl cyanoacetate furnished the corresponding ethyl

Azoles and <i>bis</i>-Azoles: Synthesis and Biological Evaluation as Antimicrobial and Anti-cancer Agents

“…On the other hand, reaction of compound 10 with 3-(2-bromoacetyl)-2H-chromen-2-one (18) under the employed condition gave the respective 2-cyano- (21) in agreement with literature 34,35) for the reaction of 2-cyano-N-aryl-3-(phenylamino) acrylamides with α-haloketones (Chart 5). The reaction proceeds via nucleophilic displacement of hydrogen bromide by thiol group to give S-alkylated intermediate 19, which underwent nucleophilic addition of (PhNH) group to carbonyl group of chromen-2-one ring to give the respective intermediate 20.…”

Synthesis of Novel 1‐Pyrazolylpyridin‐2‐ones as Potential Anti‐Inflammatory and Analgesic Agents

“…The 4-alkyl-2-oxo-1,2-dihydropyridine-3-carbonitrile 2 was obtained through a one-pot reaction of cyanoacetanilide 1 with acetaldehyde and malononitrile in ethanol / piperidine [7 -9]. On the other hand, reaction of 1 with different arylidenes in presence of piperidine as catalyst [10] afforded substituted 4-aryl-2-oxo-1,2-dihydropyridine-3-carbonitriles 3a-e. Cyclocondensation of 1 with acetyl acetone or benzoyl acetone in ethanol using catalytic amount of piperidine [8,9] furnished 1-pyrazolyl-4-methyl-2-oxo-6-substituted-1,2-dihydropyridine-3-carbonitriles 4a, b. It is important to emphasize that the presence of the nitrile group at the 3-position of the pyridone ring activates the methyl group at position 4.…”

“…Mass spectra were recorded on Varian MAT 311-A 70 eV (Varian). 2-(Arylidene) malononitrile [14] 3a was prepared according to the reported method [10]. MF: CHNO; mp.…”

Ionic Liquid Catalyzed 4,6-Disubstituted-3-Cyano-2-Pyridone Synthesis Under Solvent-Free Conditions

“…They are also used as starting materials for the synthesis of a number of fused heterocycles of biological importance such as isoxazolopyridines, pyrazolopyridines, thienopyridines and pyridoquinazolines [12]. 3-Cyano-2-pyridones can be synthesized by reaction of cyanoacetamides with 1,3-diketones [13][14][15], acrylonitrile [16,17] or a,b-unsaturated carbonyl compounds [18] in presence of various basic catalysts. Some studies have been published on synthesis of 3-cyano-2-pyridones using microwave irradiation in presence of strongly basic catalysts [19,20].…”