1131-33-5Relevant academic research and scientific papers
2-Position-Selective Trifluoromethylthiolation of Six-Membered Heteroaromatic Compounds
Muta, Ryuhei,Torigoe, Takeru,Kuninobu, Yoichiro
, (2019)
The regioselective C-H trifluoromethylthiolation of six-membered heteroaromatic compounds via nucleophilic attack of a CF3S source on the electrophilically activated six-membered heteroaromatic ring was developed. The reaction proceeds in good yield with good functional group tolerance, even on a gram-scale. The key to the successful regioselective transformation is the presence of an additive (2,4-dinitrobenzenesulfonyl chloride). The regioselective trifluoromethylthiolation of quinidine derivative is also demonstrated. Trifluoromethylthiolation, followed by S-oxidation, affords the corresponding sulfones.
Dehydrogenative etherification homocoupling of heterocyclic N-oxides
Zhang, Dong,Qiao, Kai,Yuan, Xin,Zheng, Mingwei,Fang, Zheng,Wan, Li,Guo, Kai
, p. 1752 - 1756 (2018)
A novel approach was developed for the dehydrogenative etherification homocoupling of heterocyclic N-oxides in the presence of silver oxide and PyBroP. Various substrates were well tolerated and the desired products were obtained in moderate to good yields. Generally, this reaction features excellent functional group compatibility, broad substrate scope and good regioselectivity.
Arylation of pyridine N-oxides via a ligand-free Suzuki reaction in water
Liu, Chun,Zhang, Shao-Ke,Zhang, Yi-Xia,Jin, Zi-Lin
, p. 55 - 57 (2015)
We report a practical and highly efficient protocol for the arylation of pyridine N-oxides with arylboronic acid through palladium-catalyzed Suzuki reaction in water. This ligand-free Suzuki reaction is performed in the presence of diisopropylamine and gi
Copper-Catalyzed Regioselective Cascade Alkylation and Cyclocondensation of Quinoline N-Oxides with Diazo Esters: Direct Access to Conjugated π-Systems
Biswas, Aniruddha,Karmakar, Ujjwal,Pal, Arun,Samanta, Rajarshi
, p. 13826 - 13830 (2016)
An inexpensive copper-catalyzed cascade regioselective alkylation, followed by cyclocondensation of quinoline N-oxides with α-diazo esters has been achieved successfully to provide heteroarene-containing conjugated π-systems. The developed method is simple, straightforward, and economical with a broad range of substrate scope. The dual role of copper catalyst in the C?H bond functionalization and in Lewis acid-promoted cyclization was explored.
2-Position-selective C[sbnd]H fluoromethylation of six-membered heteroaryl N-oxides with (fluoromethyl)triphenylphosphonium iodide
Hu, Chen-Chen,Hu, Wei-Qiang,Qing, Feng-Ling,Xu, Xiu-Hua
, (2021)
A mild and efficient method for the regioselective C[sbnd]H fluoromethylation of heteroaryl N-oxides with (fluoromethyl)triphenylphosphonium iodide is presented. With LiOt-Bu as the base and DMSO as the solvent, this reaction delivers a series of C2-fluor
A Photosensitizer-Free Radical Cascade for Synthesizing CF3-Containing Polycyclic Quinazolinones with Visible Light
Hu, Qiang,Yu, Wan-Lei,Luo, Yong-Chun,Hu, Xiu-Qin,Xu, Peng-Fei
supporting information, p. 1493 - 1501 (2022/02/07)
Herein, we report an efficient photoinduced radical tandem trifluoromethylation/cyclization reaction of N-cyanamide alkenes for the synthesis of functionalized quinazolinones. Importantly, the reaction is carried out under mild conditions without any addi
Copper/manganese oxide catalyzed regioselective amination of quinoline N-oxides: An example of synergistic cooperative catalysis
Sahoo, Tapan,Thakur, Dinesh,Panda, Asit Baran,Ghosh, Subhash Chandra
supporting information, (2021/09/29)
An atom economical and efficient protocol for C-2 amination of quinoline N-oxides using our synthesized recyclable heterogeneous Cu–MnO catalyst has been reported here. Direct C[sbnd]H aminations of heterocyclic N-oxides with secondary amine were carried out under base, and ligand-free conditions in good to excellent yields. The major advantage is that air is used as a sole oxidant and our catalyst is recycled several times.
Visible-Light-Induced ortho-Selective Migration on Pyridyl Ring: Trifluoromethylative Pyridylation of Unactivated Alkenes
Jeon, Jinwon,He, Yu-Tao,Shin, Sanghoon,Hong, Sungwoo
supporting information, p. 281 - 285 (2019/11/26)
The photocatalyzed ortho-selective migration on a pyridyl ring has been achieved for the site-selective trifluoromethylative pyridylation of unactivated alkenes. The overall process is initiated by the selective addition of a CF3 radical to the alkene to provide a nucleophilic alkyl radical intermediate, which enables an intramolecular endo addition exclusively to the ortho-position of the pyridinium salt. Both secondary and tertiary alkyl radicals are well-suited for addition to the C2-position of pyridinium salts to ultimately provide synthetically valuable C2-fluoroalkyl functionalized pyridines. Moreover, the method was successfully applied to the reaction with P-centered radicals. The utility of this transformation was further demonstrated by the late-stage functionalization of complex bioactive molecules.
Visible-light-promoted c2 selective arylation of quinoline and pyridine n-oxides with diaryliodonium tetrafluoroborate
Li, Dazhi,Liang, Ce,Jiang, Zaixing,Zhang, Junzheng,Zhuo, Wang-Tao,Zou, Fan-Yue,Wang, Wan-Peng,Gao, Guo-Lin,Song, Jinzhu
, p. 2733 - 2742 (2020/03/11)
A protocol of visible-light-promoted C2 selective arylation of quinoline and pyridine N-oxides, with diaryliodonium tetrafluoroborate as an arylation reagent, using eosin Y as a photocatalyst for the construction of N-heterobiaryls was presented. This met
Preparation method of 2-phenyl substituted pyridine nitrogen oxide compound
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Paragraph 0029-0038, (2020/03/09)
The invention discloses a preparation method of a 2-phenyl substituted pyridine nitrogen oxide compound, relates to a preparation method of a pyridine nitrogen oxide derivative, and aims to solve thetechnical problems of flammability, explosiveness, harsh reaction conditions and poorer regioselectivity of a catalyst in the conventional direct selective functionalization method. The method comprises the following steps: adding the pyridine nitrogen oxide derivative, diphenyl iodide tetrafluoroborate, an eosin Y catalyst, an alkali and an additive into a transparent reactor at room temperature,and sealing; replacing air in the reactor with nitrogen to form a nitrogen atmosphere, injecting a solvent, and uniformly mixing; irradiating the reactor with blue LEDs lamp light for reaction; afterthe reaction is finished, removing the solvent through rotary evaporation, and then performing separation and purification of prefabricated silica gel column chromatography to obtain the 2-phenyl substituted pyridine nitrogen oxide compound, and the structural formula of the 2-phenyl substituted pyridine nitrogen oxide compound is as shown in the specification, R1 is hydrogen, alkyl, nitrile group, halogen, phenyl or nitro; the 2-phenyl substituted pyridine nitrogen oxide compound can be used in the fields of screening of drug lead compounds or biological activity test and research.
