1613-37-2Relevant academic research and scientific papers
Conformational and structural analysis of bis(4-chloroquinoline-N-oxide)hydrogen tribromide
Romanov,Nizhnik, Ya. P.,Fofanov
, p. 365 - 369 (2015)
The X-ray diffraction and conformational study of bis(4-chloroquinoline-N-oxide)hydrogen tribromide is performed. Two conformations corresponding to the minima on the energy curve are found by DFT using the ABINIT software. The model of one of the conformers generally matches with the structure determined experimentally for this compound using X-ray diffraction. In both instances, the structure with the dihedral angle (quinoline - N-O-H) close to 90° is most favorable, which is explained in terms of resonance theory and steric factors. It is concluded that oxygen atoms in the complex are in the sp3 hybridization state and the sp2 hybrid state of the oxygen atom is not possible here due to steric factors.
Copper-catalyzed intermolecular dehydrogenative amidation/amination of quinoline N-oxides with lactams/cyclamines
Li, Gang,Jia, Chunqi,Sun, Kai
, p. 5198 - 5201 (2013)
C-H, N-H dehydrogenative coupling of quinoline N-oxides with lactams/cyclamines has been achieved in the presence of the Cu(OAc)2 catalyst to give good to excellent yields. This study provides a new strategy for the construction of a 2-aminoqui
13C NMR studies on the structure of 5H- and 6H-indolo-[2,3-b] quinolines and the related compounds
Kamieńska-Trela,Kania,Bechcicka,Kaczmarek
, p. 209 - 218 (2003)
A set of 13C NMR data which included one-bond spin-spin coupling constants has been obtained for a large series of heteroaromatic compounds. It contains, among others, 6-substituted quinolines, their N-oxides, 2- and 5-methoxyindoles. The results obtained for these basic molecules were compared with those measured for a series of variously substituted 5H- and 6H-indolo[2,3-b]quinolines, which shed new light on the electronic structure of the two latter groups of the compounds.
A fluorescence chemosensor based on imidazo[1,2-a]quinoline for Al3+ and Zn2+ in respective solutions
Sun, Junhua,Liu, Zheng,Wang, Ying,Xiao, Shihua,Pei, Meishan,Zhao, Xiuxian,Zhang, Guangyou
, p. 100873 - 100878 (2015)
A new chemosensor, N′-[(2-hydroxyphenyl)methylidene]imidazo[1,2-a]quinoline-2-carbohydrazide (L2), was developed, which could detect Al3+ in DMSO/H2O HEPES buffer and Zn2+ in EtOH/H2O HEPES buffer. The chemosensor exhibits high selectivity and sensitivity for sensing Al3+ and Zn2+ with a fluorescence "turn-on" mode.
Heterogeneous mesoporous manganese oxide catalyst for aerobic and additive-free oxidative aromatization of N-heterocycles
Mullick, Kankana,Biswas, Sourav,Angeles-Boza, Alfredo M.,Suib, Steven L.
, p. 2256 - 2259 (2017)
Herein, we report a heterogeneous, aerobic, additive-free and environmentally benign catalytic protocol for oxidative aromatization of saturated nitrogen-heterocycles using a mesoporous manganese oxide material. The aromatized products can be separated by easy filtration and the catalyst is reusable for at least four cycles. Mechanistic investigation provides evidence for radical intermediates, a multi-electron redox cycle between Mn centers, and an oxygen exchange mechanism.
Graphene oxide as an active carbocatalyst for cyanation of quinoline and isoquinoline N-Oxides
Huang, Panpan,Peng, Xiangjun,Qiu, Genhong,Yu, Keyang,Li, Hong,Kong, Lingting,Hu, Jiaming,Chen, Zhengwang,Huang, Qing,Liu, Liangxian
, (2021)
Graphene oxide was found to be a highly efficient and cost-effective heterogeneous catalyst for the direct metal-free transformation of quinoline and isoquinoline N-oxides into the corresponding nitriles under mild conditions. This method is simple, econo
Copper-Catalyzed Deoxygenative C2-Sulfonylation of Quinoline N -Oxides with DABSO and Phenyldiazonium Tetrafluoroborates for the Synthesis of 2-Sulfonylquinolines via a Radical Reaction
Deng, Qi,Dong, Dao-Qing,Li, Guang-Hui,Wang, Zu-Li,Yan, Shi-Qiang
, p. 3313 - 3319 (2019)
An efficient and practical method for the synthesis of 2-sulfonylquinolines through copper-catalyzed deoxygenative C2-sulfonylation of quinoline N -oxides with 1,4-diazabicyclo[2.2.2]octane bis(sulfur dioxide) (DABSO) and phenyldiazonium tetrafluoroborates is demonstrated. Products with various substituents were obtained in moderate to high yields.
Reductive Amination Revisited: Reduction of Aldimines with Trichlorosilane Catalyzed by Dimethylformamide─Functional Group Tolerance, Scope, and Limitations
Campbell, Joanna L. P.,Davies, Christopher D.,Ho?ek, Jan,Ko?ovsky, Pavel,Kysilka, Ond?ej,Popov, Kirill K.,Pour, Milan
, p. 920 - 943 (2022/01/27)
Aldimines, generated in situ from aliphatic, aromatic, and heteroaromatic aldehydes and aliphatic, aromatic, and heteroaromatic primary or secondary amines, can be reduced with trichlorosilane in the presence of dimethylformamide (DMF) as an organocatalys
Method for preparing sulfone and N-oxygen compound by using green and efficient oxidation system
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Paragraph 0021-0023, (2021/01/29)
The invention discloses a method for preparing sulfone and N-oxygen compound by using a green and efficient oxidation system. The method comprises the following steps of: by using a tertiary amine compound or aromatic thioether or fatty thioether compound as a raw material, H2O2 as an oxidant, methanol as a reaction solvent and potassium carbonate as an alkali, introducing sulfuryl fluoride 5O2F2gas as an accelerator; performing stirring at room temperature under a sealed condition for oxidation reaction; and after finishing the reaction, filtering to remove solid potassium carbonate, dryingto remove water, filtering to obtain a crude product, and finally carrying out column chromatography separation to obtain a pure product. Tertiary amine is oxidized into an N-oxygen compound, and thethioether is oxidized into sulfone. According to the method, the sulfuryl fluoride (SO2F2) which is very cheap and easy to obtain is used as the reaction promoter, green and environment-friendly hydrogen peroxide (H2O2) is used as an oxidizing agent, and so that the yield of the reaction is generally high; after the reaction, byproducts are only water and inorganic salts (SO4 and F) whichare easy to remove and free of pollution, and the green and efficient oxidation system can be realized, and therefore, the method is suitable for large-scale industrial production.
SO2F2-mediated oxidation of primary and tertiary amines with 30% aqueous H2O2 solution
Liao, Xudong,Zhou, Yi,Ai, Chengmei,Ye, Cuijiao,Chen, Guanghui,Yan, Zhaohua,Lin, Sen
supporting information, (2021/11/01)
A highly efficient and selective oxidation of primary and tertiary amines employing SO2F2/H2O2/base system was described. Anilines were converted to the corresponding azoxybenzenes, while primary benzylamines were transformed into nitriles and secondary benzylamines were rearranged to amides. For tertiary amine substrates quinolines, isoquinolines and pyridines, their oxidation products were the corresponding N-oxides. The reaction conditions are very mild and just involve SO2F2, amines, 30% aqueous H2O2 solution, and inorganic base at room temperature. One unique advantage is that this oxidation system is just composed of inexpensive inorganic compounds without the use of any metal and organic compounds.
