85-06-3Relevant academic research and scientific papers
Rhodium-Catalyzed C-H Annulation of Free Anilines with Vinylene Carbonate as a Bifunctional Synthon
Nan, Jiang,Yin, Jiacheng,Gong, Xue,Hu, Yan,Ma, Yangmin
supporting information, p. 8910 - 8915 (2021/11/24)
Chemical transformation with vinylene carbonate as an emerging synthetic unit has recently attracted considerable attention. This report is a novel conversion pattern with vinylene carbonate, in which such a vibrant reagent unprecedentedly acts as a difunctional coupling partner to complete the C-H annulation of free anilines. From commercially available substrates, this protocol leads to the rapid construction of synthetically versatile 2-methylquinoline derivatives (43 examples) with excellent functionality tolerance.
A ortho position alkylation method of organic compound containg pyridine
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Paragraph 0108-0116, (2020/12/05)
A process for introducing alkyl at ortho positions of organic compounds containing pyridine. The method is not affected by the kind of substituent bonded to the pyridine and can be alkylated with high positional selectivity and high yield at N-based ortho-position of pyridine without being affected by the kind of substituent introduced to pyridine ortho position (pyridine N-based) can be advantageously used for the preparation of a compound containing an alkyl-introduced pyridine structure.
C2-Selective C-H methylation of heterocyclic N-oxides with sulfonium ylides
An, Won,Choi, Su Bin,Kim, Namhoon,Kwon, Na Yeon,Ghosh, Prithwish,Han, Sang Hoon,Mishra, Neeraj Kumar,Han, Sangil,Hong, Sungwoo,Kim, In Su
supporting information, p. 9004 - 9009 (2020/11/30)
A redox-neutral C2-selective methylation of heterocyclic N-oxides with sulfonium ylides is described herein. This report presents unprecedented findings for the utility of sulfonium ylides as the methylation source of N-heterocycles beyond the Corey-Chaykovsky reaction. Intriguingly, pyrrolidine plays a significant role in minimizing the reductive C2-methylation process. This method is characterized by its mild conditions, simplicity, and excellent site selectivity. The applicability of the developed protocol is showcased by the late-stage methylation and sequential transformations of complex drug molecules.
Reductive C2-Alkylation of Pyridine and Quinoline N-Oxides Using Wittig Reagents
Han, Sangil,Chakrasali, Prashant,Park, Jihye,Oh, Hyunjung,Kim, Saegun,Kim, Kyuneun,Pandey, Ashok Kumar,Han, Sang Hoon,Han, Soo Bong,Kim, In Su
supporting information, p. 12737 - 12740 (2018/09/20)
The ability to alkylate pyridines and quinolines is important for their further development as pharmaceuticals and agrochemicals, and for other purposes. Herein we describe the unprecedented reductive alkylation of pyridine and quinoline N-oxides using Wittig reagents. A wide range of pyridine and quinoline N-oxides were converted into C2-alkylated pyridines and quinolines with excellent site selectivity and functional-group compatibility. Sequential C?H functionalization reactions of pyridine and quinoline N-oxides highlight the utility of the developed method. Detailed labeling experiments were performed to elucidate the mechanism of this process.
Assembly of Diversely Substituted Quinolines via Aerobic Oxidative Aromatization from Simple Alcohols and Anilines
Li, Jixing,Zhang, Jinlong,Yang, Huameng,Jiang, Gaoxi
supporting information, p. 3284 - 3290 (2017/03/23)
An aerobic oxidative aromatization of simple aliphatic alcohols and anilines under the Pd(OAc)2/2,4,6-Collidine/Br?nsted acid catalytic system has been established, providing a direct approach for the preparation of diverse substituted quinoline derivatives in high yields with wide functional group tolerance. Practically, the protocol can be easily scaled up to gram-scale and was utilized in the concise formal synthesis of a promising herbicide candidate.
Organo-Photoredox Catalyzed Oxidative Dehydrogenation of N-Heterocycles
Sahoo, Manoj K.,Jaiswal, Garima,Rana, Jagannath,Balaraman, Ekambaram
supporting information, p. 14167 - 14172 (2017/10/16)
We report here for the first time the catalytic oxidative dehydrogenation of N-heterocycles by a visible-light organo-photoredox catalyst with low catalyst loading (0.1–1 mol %). The reaction proceeds efficiently under base- and additive-free conditions with ambient air at room temperature. The utility of this benign approach is demonstrated by the synthesis of various pharmaceutically relevant N-heteroarenes such as quinoline, quinoxaline, quinazoline, acridine, and indole.
A Convenient Procedure for the Oxidative Dehydrogenation of N-Heterocycles Catalyzed by FeCl2/DMSO
Zhou, Weiyou,Taboonpong, Piyada,Aboo, Ahmed Hamdoon,Zhang, Lingjuan,Jiang, Jun,Xiao, Jianliang
supporting information, p. 1806 - 1809 (2016/07/16)
A convenient catalytic procedure has been developed for the oxidative dehydrogenations of N-heterocycles. Combining catalytic FeCl2 with DMSO yields a catalyst that promotes the dehydrogenation of tetrahydroquinolines and related heterocycles under 1 bar of O2, affording the corresponding N-heteroaromatic products in moderate yields.
Direct functionalization of benzoquinolines
Mamane, Victor,Louerat, Frederic,Fort, Yves
experimental part, p. 90 - 93 (2010/09/18)
The first direct lithiation of the pyridine ring of benzo[h]- and benzo[f]- quinolines is reported. The method allowed the introduction of different electrophiles (Cl, Br and SPh) in 2-position. Other groups were introduced by direct nucleophilic addition of alkyllithiums allowing further transformations to functional groups such as esters and thiolesters.
