Synthesis, properties, and biological activity of 3-pyridylamides of 4-aryl-2-hydroxy-4-oxo-2-butenic (aroylpyruvic) acids

(Het)aroylpyruvic acids and their derivatives as promising building blocks for organic synthesis

“…Of transformations of (H)AP on treatment with C,N-dinucleophiles, the reactions with ethyl 3-aminocrotonate and cyanoacetamide are documented. Under mild conditions (at 20 8C in the absence of bases), the pyruvate 2a adds ethyl 3-aminocrotonate at the b-diketone fragment to give 3,4-bis(ethoxycarbonyl)-2-methyl-6phenylpyridine (62). 105 The most electrophilic centre of AP [the C( 2) atom] reacts with the C-nucleophilic centre of the crotonate and the C(4) atom reacts with the amino group.…”

“…149 Unlike the APA 4 and their esters 2, the APA arylamides 6 react with PDA to give, depending on the reaction conditions, 4-arylbenzo[b]-1,4-diazepine-2-carboxylic acid arylamides 91 29,151 instead of the expected quinoxalinones 86, 115 or a mixture of these products. 62,149 The formation of the quinoxalinones 86 is promoted by performing the reaction in EtOH ± AcOH ± H 2 O ± HCl mixtures at pH 2.4 ± 4.6 and temperatures of 20 ± 65 8C. 115 Meanwhile, short-term fusion of the reactants at 115 ± 130 8C furnishes predominantly the benzodiazepines 91.…”

“…(Het)aroylpyruvic acids and their derivatives as promising building blocks for organic synthesis mixture affords both the quinoxalinone 86a and the benzodiazepine 91 (R = 3-pyridyl). 62 86: Ar = XC6 H4 (X = H, 4-Me, 4-OMe, 4-Cl, 4-Br, 4-NO2, 3-NO2); 91: Ar = 4-XC6H4 (X = H, Me, OMe, Br); R = 4-YC6H4 (Y = H, Me, OMe, Br), 3-pyridyl.…”

N-(2-Chloro-5-cyanophenyl)-4,4,4-trifluorobutanamide

“…

4, was synthesized by reacting 4,4,4-trifluorobutanoic acid (1) with 2-amino-4-chlorobenzonitrile (2) in the presence of triethylamine and propylphosphonic anhydride in ethyl acetate. Characterization of the compound was done by IR, 1 H-NMR, 13 C-NMR, LC-MS and CHN analysis.

…”

“…Amides bearing a trifluoromethyl substituent show a broad spectrum of pharmacological properties, including antitumour [1], anti-inflammatory [2], antioxidant [3], analgesic [4] and antiviral activity [5]. It was also reported that substituted amides show higher anticonvulsive [6], hypoglycemic [7], antiarrhythmic [8] and fungicidal activity [9].…”