- A facile solid-phase synthesis of 3,4,6-trisubstituted-2-pyridones using sodium benzenesulfinate as a traceless linker
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A facile and traceless solid-phase synthesis of 3,4,6-trisubstituted-2- pyridones has been developed using polystyrene sodium benzenesulfinate resin. The chemistry is applicable to combinatorial library synthesis.
- Li, Weiwei,Chen, Yu,Lam, Yulin
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- Synthesis and Photophysical Properties of 3-Amino-4-arylpyridin-2(1 H)-ones
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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.
- Abramov, Anton A.,Chernenko, Sergey A.,Fisyuk, Alexander S.,Kostyuchenko, Anastasia S.,Shatsauskas, Anton L.
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p. 227 - 238
(2019/12/28)
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- Synthesis of 3-amino-6-methyl-4-phenylpyridin-2(1H)-one and its derivatives
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[Figure not available: see fulltext.] A reaction of 2-cyanoacetamide with benzylideneacetone in DMSO containing potassium tert-butoxide was used to synthesize 3-cyano-6-methyl-4-phenylpyridin-2(1H)-one, which was converted by acidic hydrolysis to 6-methyl-2-oxo-4-phenyl-1,2-dihydropyridine-3-carboxamide. A Hofmann reaction of this compound in the presence of sodium hypobromite led to 3-amino-5-bromo-6-methyl-4-phenylpyridin-2(1H)-one, while its treatment with calcium hypochlorite produced 5-methyl-7-phenyloxazolo[5,4-b]pyridin-2(1H)-one. The latter compound was converted by heating with alkali to 3-amino-6-methyl-4-phenylpyridin-2(1H)-one, which gave azomethine in a reaction with benzaldehyde, while N-acylated derivatives were obtained in reactions with acyl halides. The heating of N1,N2-bis(6-methyl-2-oxo-4-phenyl-1,2-dihydropyridin-3-yl)oxalylamide in the presence of POCl3 allowed to obtain 5,5'-dimethyl-7,7'-diphenyl-2,2'-bis-(oxazolo[5,4-b]pyridine).
- Shatsauskas, Anton L.,Abramov, Anton A.,Saibulina, Elina R.,Palamarchuk, Irina V.,Kulakov, Ivan V.,Fisyuk, Alexander S.
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p. 186 - 191
(2017/05/19)
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- One-Pot Synthesis of 3-Cyano-2-pyridones
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A versatile synthesis of 3-cyano-2-pyridones via a one-pot, four-component condensation of ethyl cyanoacetate, ketones, aldehydes, and ammonium acetate under very mild conditions has been developed. This method provides rapid access to this type of valuab
- Wang, Yingcai,Liu, Gang,Reyes, Jeremy Chris P.,Duverna, Randolph
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p. 1185 - 1191
(2015/08/06)
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- Cascade synthesis of 2-pyridones using acrylamides and ketones
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Microwave assisted non-catalytic condensation of 2-cyanoacetamide with aromatic aldehydes, and enolate mediated Michael-type addition to acrylamide followed by oxidative cyclization, produce 2-pyridones in good to excellent yield. Unsymmetrical ketones produce two regioisomeric enolates, therefore thermodynamic and kinetic products of butan-2-one and pentan-2-one have been isolated and fully characterized. This journal is
- Rai, Sunil K.,Khanam, Shaziya,Khanna, Ranjana S.,Tewari, Ashish K.
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p. 44141 - 44145
(2015/02/02)
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- AZAINDAZOLES
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Herein are disclosed azaindazoles of formula (I), (I), where the various groups are defined herein, and which are useful for treating cancer.
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Page/Page column 53; 54
(2013/03/28)
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- Solvent and structural effects on the UV-Vis absorption spectra of some 4,6-disubstituted-3-cyano-2-pyridones
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A series of 4,6-disubstituted-3-cyano-2-pyridones was synthesized and their UV-Vis absorption spectra were recorded in the region 200-600 nm in the set of selected solvents. The effects of solvent dipolarity/polarizability and solvent-solute hydrogen-bonding interactions on the spectral shifts were analyzed by means of the linear solvation energy relationship concept of Kamlet and Taft. The influence of solvents as well as substituents on the 2-pyridone/2-hydroxypyridine tautomeric equilibration was evaluated. The absorption band maximum of the 2-hydroxypyridine form is found to appear at a shorter wavelength than that of the 2-pyridone form in all investigated solvents. The replacement of the methyl and phenyl groups at position 6 of the pyridone ring, by a hydroxy group, significantly changes the solvatochromic behavior of the investigated pyridones.
- Alimmari, Adel S. A.,Bozic, Bojan Crossed D Sign.,Marinkovic, Aleksandar D.,Mijin, Dusan Z.,Uscumlic, Gordana S.
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p. 1825 - 1835
(2013/04/24)
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- Reaction of 4-Phenylbut-3-en-2-one with Cyanoacetamide in2:1 Ratio
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The reaction of 4-phenylbut-3-en-2-one with cyanoacetamide is not confined to a 1:1 reaction .The reaction of 2 mole equivalents of 4-phenylbut-3-en-2-one with one of cyanoacetamide
- O'Callaghan, Conor N.,McMurry, T. Brian H.,Cardin, Cristine J.,Wilcock, Deborah J.
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p. 2479 - 2486
(2007/10/02)
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- Ring Transformation Reactions of 1-Substituted 2(1H)-Pyrimidinones and Related Compounds with Active Methylene Compounds
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1-Substituted 2(1H)-pyrimidinones (I) underwent ring transformation with malononitrile and ethyl acetoacetate in the presence of sodium ethoxide to give 2-amino-3-pyridinecarbonitriles (II-VII) and N-(substituted)amino-3-pyridinecarboxylic acids (XIV and XV), respectively.Further, I reacted with ethyl cyanoacetate, dialkyl malonate, or ethyl benzoylacetate to give pyridine derivatives (VIII-XIII) bearing various functional groups at the C-3 position.The reaction of 1-substituted 2(1H)-pyrimidinethiones and 4,6-dimethyl-1-phenyl-2-phenylimino-1,2-dihydropyrimidine with active methylene compounds is also discussed.Keywords - ring transformation; 1-substituted 2(1H)-pyrimidinone; 1-substituted 2(1H)-pyrimidinethione; active methylene compound; sodium alkoxide; pyridine derivative.
- Katoh, Akira,Omote, Yoshimori,Kashima, Choji
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p. 2942 - 2946
(2007/10/02)
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