14045-37-5Relevant academic research and scientific papers
Enaminones as building blocks in heterocyclic syntheses: Reinvestigating the product structures of enaminones with malononitrile. A novel route to 6-substituted-3-oxo-2,3-dihydropyridazine-4-carboxylic acids
Alnajjar, Abdul-Aziz,Abdelkhalik, Mervat Mohammed,Al-Enezi, Amal,Elnagdi, Mohamed Hilmy
, p. 68 - 77 (2009)
The reported structures of reaction products of enaminones with malononitrile in ethanolic piperidine are revised. A novel route to 2,3-dihydropyridazine-4-carboxylic acids 4a-c via reactions of 2-cyano-5-(dimethylamino)-5-arylpenta-2,4-dienamides 8a-c wi
A one-step preparation of functionalized 3-cyano-2-pyridones
Jain, Rajul,Roschangar, Frank,Ciufolini, Marco A.
, p. 3307 - 3310 (1995)
Reaction of various enones and enals with cyanoacetamide in DMSO-tBuOK under an oxygen atmosphere furnishes 3-cyanopyridones directly and in good yield.
Synthesis and Photophysical Properties of 3-Amino-4-arylpyridin-2(1 H)-ones
Abramov, Anton A.,Chernenko, Sergey A.,Fisyuk, Alexander S.,Kostyuchenko, Anastasia S.,Shatsauskas, Anton L.
, p. 227 - 238 (2019/12/28)
A method has been developed for the preparation of oxazolo-[5,4- b ]pyridin-2(1 H)-ones based on the Hoffmann reaction of 2-oxo-1,2-dihydropyridine-3-carboxamides. Hydrolysis of oxazolo[5,4- b ]pyridin-2(1 H)-ones and the Hoffmann reaction of 2-oxo-1,2-dihydropyridine-3-carboxamides yielded 3-aminopyridin-2(1 H)-ones, including 4-aryl substituted derivatives in the series, for which effective phosphors with a quantum yield of up to 0.78 were detected. Photophysical properties of 3-aminopyridin-2(1 H)-ones were studied by UV and luminescence spectroscopy methods, and the relationship between their structure and photophysical properties was revealed.
INHIBITORS OF THE PD-1/PD-L1 PROTEIN/PROTEIN INTERACTION
-
Page/Page column 32; 33, (2017/08/01)
The present invention provides novel compounds of formula (I) that are useful as inhibitors of the PD-1/PD-L1 protein/protein interaction.
Ionic liquid catalyzed 4,6-disubstituted-3-cyano-2-pyridone synthesis under solvent-free conditions
Chavan, Sunil S.,Degani, Mariam S.
experimental part, p. 1693 - 1697 (2012/03/11)
A green protocol for the synthesis of 4,6-disubstituted-3-cyano-2-pyridones from cyanoacetamides and 1,3-dicarbonyl compounds or chalcones using guanidine based ionic liquid as catalyst has been developed. In solvent-free conditions at 30 °C, [TMG][Lac] (1,1,3,3-tetramethylguanidine lactate) was found to have the highest catalytic activity among the ionic liquids including [TMG][Ac] (1,1,3,3-tetramethylguanidine acetate), [TMG][Pr] (1,1,3,3-tetramethylguanidine propionate), [TMG][n-Bu] (1,1,3,3-tetramethylguanidine n-butyrate) and [TMG][TFA] (1,1,3,3-tetramethylguanidine trifluoroacetate). The catalyst was recovered and recycled several times without significant loss of catalytic activity. Graphical Abstract: [Figure not available: see fulltext.]
1-Substituted 3-Dimethylaminoprop-2-en-1-ones as Building Blocks in Heterocyclic Synthesis: Routes to 6-Aryl and 6-Heteroaryl-2H-pyran-2-ones and 6- and 4-Aryl-pyridin-2(1H)-ones
Al-Omran, Fatima,Al-Awadhi, Nouria,Khalik, Mervat Mohammed Abdel,Kaul, Kamini,EL-Khair, Adel Abu,Elnagdi, Mohammed Hilmy
, p. 601 - 615 (2007/10/03)
Several new 6-substituted-3-acylamino-2H-pyran-2-ones 6 a-j are prepared from the reaction of the enaminones 4 a-f with N-acyl- and N-benzoyl-glycines. The enaminones 4 a-c react with malononitrile in ethanol solution and in presence of a base to yield th
Nonpeptidic inhibitors of human leukocyte elastase. 2. Design, synthesis, and in vitro activity of a series of 3-amino-6-arylopyridin-2-one trifluoromethyl ketones
Damewood Jr.,Edwards,Feeney,Gomes,Steelman,Tuthill,Williams,Warner,Woolson,Wolanin,Veale
, p. 3303 - 3312 (2007/10/02)
A series of potent nonpeptidic inhibitors of the enzyme human leukocyte elastase (HLE) is reported. These inhibitors contain a 3-amino-2-pyridone ring as a central template in which the pyridone carbonyl and 3-position NH group are thought to form important hydrogen bonding interactions with the Val-216 residue of HLE. Substitution of the 6-position of the pyridone ring by various alkyl and aryl groups was found to afford increases in the in vitro potency of these inhibitors. A 6-position phenyl group, compound 10f, was found to result in a large increase in binding affinity, which was not obtained when the phenyl group was placed in either the 4- or 5-position of the molecule. Compound 10f was found to have good selectivity for HLE over other proteolytic enzymes, with the exception of bovine pancreatic chymotrypsin (BPC). Substitution of the 6-phenyl group in these molecules was found to decrease binding affinity for BPC without adversely affecting affinity for HLE.
A Simple Synthesis of Amphimedine
Prager, Rolf H.,Tsopelas, Chris,Heisler, Teresa
, p. 277 - 285 (2007/10/02)
The marine alkaloid amphimedine has been synthesized by a short sequence of reactions commencing from the known indenopyridinedione (2).Reaction with 4-pyridillithium, followed by hydrazoic acid treatment, gave 5-(4-pyridyl)-3,6-phenanthrolin-4(3H)-one (1
A 'Biogenetic Like' Synthesis of Perloline, 6-(3,4-dimethoxyphenyl)-5-hydroxy-5,6-dihydrobenzonaphthyridin-4(3H)-one
Duong, Thach,Prager, Rolf H.,Were, Stephen T.
, p. 1431 - 1440 (2007/10/02)
9H-Indenopyridine-1(2H),9-dione, prepared by a new efficient route, reacts with 3,4-dimethoxyphenyllithium to form the keto alcohol (7), which rearranges with hydrazoic acid to form 5-(3,4-dimethoxyphenyl)benznaphthyridin-4(3H)-one.The N-oxide photolyses smoothly to yield dehydroperloline as the sole product.
A Siple and Efficient Synthesis of 3-Cyano-4-phenyl-2-pyridone
Marecki, Paul E.,Wemple, James N.,Butke, Gregory P.
, p. 1247 - 1248 (2007/10/02)
A preparatively useful method for the synthesis of 3-cyano-4-phenyl-2-pyridone (I) is described.Reaction of 2-cyano-3-methylcinnamamide (VII) with N,N-dimethylformamide dimethyl acetal affords the corresponding dimethylaminomethylidene amide VIII which in
