Dataset Information

N-Arylation of 3-Formylquinolin-2(1H)-ones Using Copper(II)-Catalyzed Chan-Lam Coupling.

ABSTRACT: 3-formyl-2-quinolones have attracted the scientific community's attention because they are used as versatile building blocks in the synthesis of more complex compounds showing different and attractive biological activities. Using copper-catalyzed Chan-Lam coupling, we synthesized 32 new N-aryl-3-formyl-2-quinolone derivatives at 80 °C, in air and using inexpensive phenylboronic acids as arylating agents. 3-formyl-2-quinolones and substituted 3-formyl-2-quinolones can act as substrates, and among the products, the p-methyl derivative 9a was used as a substrate to obtain different derivatives such as alcohol, amine, nitrile, and chalcone.

SUBMITTER: Valencia J

PROVIDER: S-EPMC9735505 | biostudies-literature | 2022 Nov

REPOSITORIES: biostudies-literature

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N-Arylation of 3-Formylquinolin-2(1H)-ones Using Copper(II)-Catalyzed Chan-Lam Coupling.

Valencia Jhesua J Sánchez-Velasco Oriel A OA Saavedra-Olavarría Jorge J Hermosilla-Ibáñez Patricio P Pérez Edwin G EG Insuasty Daniel D

Molecules (Basel, Switzerland) 20221130 23

3-formyl-2-quinolones have attracted the scientific community's attention because they are used as versatile building blocks in the synthesis of more complex compounds showing different and attractive biological activities. Using copper-catalyzed Chan-Lam coupling, we synthesized 32 new N-aryl-3-formyl-2-quinolone derivatives at 80 °C, in air and using inexpensive phenylboronic acids as arylating agents. 3-formyl-2-quinolones and substituted 3-formyl-2-quinolones can act as substrates, an ...[more]

PMID: 36500438

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Project description:Development of heterogeneous catalysts from biomass-derived activated carbon is a challenging task. Biomass-derived activated carbon possesses a large specific surface area, highly porous structure, and good thermal/chemical stability. Magnetic copper catalysts based on biomass-derived activated carbon exhibited good catalytic activity in base-free Chan-Lam coupling and oxidations. Herein, biomass-derived activated carbon was prepared by the carbonization of neem dead leaves (abundant waste biomass) followed by chemical activation with KOH. Such a porous carbon material was used as a low cost and highly efficient support material for the preparation of inexpensive and environmentally benign magnetic catalysts [Cu@KF-C/MFe2O4, M = Co, Cu, Ni, and Zn]. In addition, KF modification was done to impart basic character to the catalyst that can perform C-N coupling under base-free conditions. Initially, Brunauer-Emmett-Teller (BET) analysis of the synthesized catalysts was carried out, which indicated that Cu@KF-C/CoFe2O4 possess more surface area as well as pore volume, and so accounting for the highest activity among the other synthesized catalysts. Further, X-ray photoelectron spectroscopy (XPS) analysis was performed, which inferred that Cu@KF-C/CoFe2O4 contains most of the copper in reduced form, i.e., Cu(0), which is the active species responsible for better catalytic activity toward Chan-Lam coupling reactions as well as oxidation of alcohols and hydrocarbons. The physiochemical properties of the most active catalyst, Cu@KF-C/CoFe2O4, was examined by BET, XPS, Fourier transform infrared Spectroscopy (FTIR), thermogravimetric analysis (TGA), field emission gun scanning electron microscopy (FEG-SEM), high-resolution transmission electron microscopy (HR-TEM), energy dispersive X-ray (EDX) mapping, energy dispersive X-ray (EDX), inductively coupled plasma atomic emission spectroscopy (ICP-AES), powder X-ray diffraction (XRD), and vibrating sample magnetometry (VSM). Moreover, Cu@KF-C/CoFe2O4 shows excellent stability as well as reusability and could be easily separated with the help of an external magnet.

Dataset Information

N-Arylation of 3-Formylquinolin-2(1H)-ones Using Copper(II)-Catalyzed Chan-Lam Coupling.

Publications

<i>N</i>-Arylation of 3-Formylquinolin-2(1<i>H</i>)-ones Using Copper(II)-Catalyzed Chan-Lam Coupling.

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