39260-15-6Relevant academic research and scientific papers
Reaction of Acylpyruvic Acids and Their Esters with N-(2-Aminophenyl)acetamide
Stepanova,Dmitriev,Maslivets
, p. 402 - 405 (2019/05/16)
Acylpyruvic acids and their esters regioselectively reacted with N-(2-aminophenyl)acetamide to give acyclic enamines, substituted (Z)-2-[(2-acetamidophenyl)amino]-4-oxobut-2-enoates, whose structure was confirmed by X-ray analysis. These compounds were formed as a result of condensation involving the primary amino group of N-(2-aminophenyl)acetamide at the most electrophilic C2=O carbonyl group of acylpyruvic acid or its ester. The obtained enamines underwent thermal heterocyclization to (Z)-3-(2-oxoethylidene)-3,4-dihydroquinoxalin-2(1H)-ones having no substituent on the N1 atom rather than expected (Z)-1-acetyl-3-(2-oxoethylidene)-3,4-dihydroquinoxalin-2(1H)-ones. The heterocyclization involves intramolecular exchange between the amide and carboxylic acid (ester) fragments. The described transformations occur under mild conditions, require no catalyst or other additives, and therefore conform to the “green chemistry” principles. The products may be interesting from the viewpoints of medicinal chemistry, pharmacology, and fine organic synthesis.
Examining the binding mechanism of 3,4-dihydro-3-(2-oxo-2-phenylethylidene) -quinoxalin-2(1H)-one and its fragments to Cu2+
Korin, Efrat,Cohen, Beny,Liu, Yong-Dong,Zeng, Cheng-Chu,Shames, Alexander I.,Becker, James Y.
, p. 2351 - 2366 (2013/08/23)
The structure and stoichiometries of the complexes that could be formed between Cu2+ and 3,4-dihydro-3-(2-oxo-2-phenylethylidene)-quinoxalin- 2(1H)-one (1) were investigated by various spectral techniques such as IR, fluorescence, UV-vis and el
Study on the structureeproperty relationship in a series of novel BF2 chelates with multicolor fluorescence
Yao, Qi-Chao,Wu, Ding-Er,Ma, Ru-Zheng,Xia, Min
, p. 1 - 9 (2013/10/08)
A series of multicolor fluorescent N,O-bidentate BF2 complexes with variable ligand structures have been synthesized. These complexes exhibit the solvent-independent optical properties and large Stoke shifts. The electrochemical measurements demonstrate that all these chelates are better electron acceptors than the commonly used material Alq3. A qualitative structureeproperty relationship among these complexes has been established on the ground of the experimental data along with the density functional theory (DFT) calculations. The theoretically calculated results are in good agreement with those obtained by the experimental determinations.
Five-membered 2,3-dioxoheterocycles: LXXIII. Synthesis and thermolysis of 3-acylpyrrolo[1,2-a]quinoxaline-1,2,4(5H)-triones
Mashevskaya,Mokrushin,Bozdyreva,Maslivets
experimental part, p. 253 - 257 (2011/05/03)
Reactions of (Z)-3-(phenacylidene-2-oxo)-3,4-dihydroquinoxalin-2(1H)-ones and (Z)-3-(3,3-dimethyl-2-oxobutylidene)-3,4-dihydroquinoxalin-2(1H)-one with oxalyl chloride led to the formation of 3-acyl-1Hpyrrolo[1,2-a]quinoxaline-1,2, 4(5H)-triones that at the thermal decarbonylation generated acyl(3- oxoquinoxalin-2-yl)ketenes which underwent the intramolecular stabilization giving 3-acylfuro[3,2-b]quinoxalin-2(4H)-ones.
Five-membered 2,3-dioxo heterocycles: LXVI. Reactions of (2Z,5Z)-1-aryl-3-hydroxy-5-[3,3-dimethyl-3,4-dihydroisoquinolin-1(2H)-ylidene] pent-2-ene-1,4-diones with o-phenylenediamine and hydrazine. Crystalline and molecular structure of 2-{(Z)-8,8-dimethyl
Khalturina,Shklyaev,Aliev,Maslivets
experimental part, p. 1519 - 1522 (2010/03/26)
(2Z,5Z)-1-Aryl-3-hydroxy-5-[3,3-dimethyl-3,4-dihydroisoquinolin-1(2H) -ylidene]pent-2-ene-1,4-diones reacted with o-phenylenediamine and hydrazine to give 3-[(Z)-2-aryl-2-oxoethylidene]-1,2,3,4-tetrahydroquinoxalin-2-ones and 1-(3-aryl-1H-pyrazol-5-yl)-2-
Sulfamic acid as an effective catalyst in solvent-free synthesis of β-enaminoketone derivatives and X-ray crystallography of their representatives
Xia, Min,Wu, Bin,Xiang, Guo-Feng
, p. 1268 - 1278 (2008/09/18)
Two types of β-enaminoketone derivatives of 3-(2-oxo-2-arylethylidene) -3,4-dihydro-1H-quinoxalin-2-ones and 3-(2-oxo-2-arylethylidene)-3,4-dihydro- benzo[1,4]oxazin-2- ones were effectively and conveniently prepared in good to excellent yields under solv
Reactions of acylpyruvic acids and 2,3-dihydrofuran-2,3-diones with 2,3-diaminopyridine
Sof'ina,Igidov,Koz'minykh,Trapeznikova,Kasatkina,Koz'minykh
, p. 1017 - 1025 (2007/10/03)
Acylpyruvic acids readily react with 2,3-diaminopyridine to form (Z)-3-acylmethylene-1H-3,4-dihydropyrido[2,3-b]pyrazin-2-ones. 5-Aryl-2,3-dihydrofuran-2,3-diones which can be regarded as lactones derived from γ-enolized aroylpyruvic acids react with 2,3-diaminopyridine under mild conditions, yielding regioisomeric (Z)-2-aroylmethylene-4H-1,2-dihydropyrido[2,3-b]pyrazin-3-ones. The structure of the products and reaction chemoselectivity are discussed.
