78941-89-6Relevant academic research and scientific papers
Palladium-Catalyzed Three-Component Cascade Reaction of Nitriles: Synthesis of 2-Arylquinoline-4-carboxylates
Zhao, Zhiwei,Zeng, Ge,Chen, Yinan,Zheng, Jinming,Chen, Zhongyan,Shao, Yinlin,Zhang, Fangjun,Chen, Jiuxi,Li, Renhao
, p. 7955 - 7960 (2021/10/20)
A new method for converting easy availability starting materials 2-(2-oxoindolin-3-yl)acetonitrile, arylboronic acids, and alcohols into 2-arylquinoline-4-carboxylates is reported. The procedure involves a three-component addition/ring expansion/esterification reaction in the presence of Pd(II) catalyst with high functional group tolerance under mild conditions. In addition, the photophysical properties of the resulting product were investigated and exhibited excellent polarity-sensitive fluorescence properties and AIE property.
Microwave-assisted synthesis of 3,1-benzoxazin-2-ones from 3-hydroxyoxindoles
Suarez-Castillo, Oscar R.,Bautista-Hernandez, Claudia I.,Sanchez-Zavala, Maricruz,Melendez-Rodriguez, Myriam,Sierra-Zenteno, Araceli,Morales-Rios, Martha S.,Joseph-Nathan, Pedro
, p. 2147 - 2171,25 (2020/08/31)
A general protocol for the synthesis of 3,1-benzoxazin-2-ones 18 from 3-hydroxyoxindoles 16 in a two steps sequence through phenylsuccinates or phenylpropionates 17 is described. Best reaction conditions for ring opening of 16 to succinates or propionates 17 were achieved using alcohol/silica gel, while cyclization of 17 to benzoxazinones 18 was easily done with HCl/alcohol. It was also found that 17 and 18 can be transesterified using HCl/alcohol. Most transformations were carried out by traditional heating and by microwave (MW) irradiation to accelerate reaction rates.
Convergent synthesis of dihydroquinolones from o-aminoarylboronates
Horn, Joachim,Li, Ho Yin,Marsden, Stephen P.,Nelson, Adam,Shearer, Rachel J.,Campbell, Amanda J.,House, David,Weingarten, Gordon G.
experimental part, p. 9002 - 9007 (2009/12/22)
An efficient and convergent one-step synthesis of substituted dihydroquinolin-2-ones from α,β-unsaturated esters and aminoaryl pinacolboronates under rhodium catalysis is reported. The reaction is easily applicable in parallel synthesis format and provide
Structural characterization of isomeric methyl 2-(2-oxo-3-indolyl)acetate and methyl 1-(2-oxo-4-quinolyl)formate
Rivera-Becerril, Ernesto,Perez-Hernandez, Nury,Joseph-Nathan, Pedro,Morales-Rios, Martha S.
, p. 1459 - 1466 (2007/10/03)
Crystalline and amorphous forms of methyl 2-(2-oxo-3-indolyl)acetate (1) were obtained showing significant differences in their melting points. The X-ray structure for the trigonal polymorph is reported. In addition, oxindole (1) was easily acid-catalyzed ring enlarged to give the structural isomer quinolone (2) for which the crystal structure was also determined. These results resolve several chemical inquiries related to the structural characterization of 1 and 2.
Dimethyl malonate as a one-carbon source: A novel method of introducing carbon substituents onto aromatic nitro compounds
Selvakumar,Yadi Reddy,Sunil Kumar,Iqbal, Javed
, p. 8395 - 8398 (2007/10/03)
A number of carbon substituents possessing various functional groups could be introduced onto aromatic nitro compounds using dimethyl malonate as a one-carbon source and linker. Decarboxylation of both the ester groups originating from dimethyl malonate in this methodology is particularly significant.
Electrochemical Carboxylation of Some Heteroaromatic Compounds
Fuchs, Peter,Hess, Ulrich,Holst, Hans Henrik,Lund, Henning
, p. 185 - 192 (2007/10/02)
Thirty heteroaromatic compounds have been investigated by cyclic voltammetry (CV) and/or preparative scale electrolysis (PSE) in the absence and presence of carbon dioxide.The rate constants of dehalogenation of the primarily formed anion radical of halogenated heterocycles were estimated from cyclic voltammetric data; these data indicated that carboxylation without loss of chlorine is possible under cyclic voltammetric conditions when the rate constant of cleavage is less than about 104 s-1.PSE confirmed that such halogenated heterocycles may be reductively carboxylated without loss of halogen.In the competition between cleavage and carboxylation low temperatures favour the latter reaction.
