63124-13-0Relevant articles and documents
Ru(III)-catalyzed construction of variously substituted quinolines from 2-aminoaromatic aldehydes (ketones) and isoxazoles: Isoxazoles as cyclization reagent and cyano sources
Cui, Xiuling,Han, Xiliang,Hu, Di,Hu, Wei,Pi, Chao,Wu, Yangjie
, (2022/01/28)
A Ru(Ⅲ)-catalyzed annulation reaction of 2-aminoaromatic aldehydes (ketones) and isoxazoles to afford diverse 3-cyanoquinolines has been developed. Notably, isoxazole acted as a cyclization reagent and nontoxic cyano source via N-O bond cleavage and fragm
Regioselective Reaction of Heterocyclic N-Oxides, an Acyl Chloride, and Cyclic Thioethers
Frei, Przemyslaw,Heulyn Jones,Kay, Steven T.,McLellan, Jayde A.,Johnston, Blair F.,Kennedy, Alan R.,Tomkinson, Nicholas C. O.
, p. 1510 - 1517 (2018/02/10)
Treatment of electron deficient pyridine N-oxides with 4-nitrobenzoyl chloride and a cyclic thioether in the presence of triethylamine leads to the corresponding 2-functionalized product in up to a 74% isolated yield. The transformation can also be accomplished with alternative nitrogen containing heterocycles, including quinolines, pyrimidines, and pyrazines. To expand the scope of the transformation, diisopropyl ether can be used as the reaction medium to allow for the use of solid thioether substrates.
Stable annelated chiral NADH models with a rigidified amide part in the quinoline series: Synthesis, reactivity and grafting on a Merrifield resin
Vitry, Christiane,Vasse, Jean-Luc,Dupas, Georges,Levacher, Vincent,Quéguiner, Guy,Bourguignon, Jean
, p. 3087 - 3098 (2007/10/03)
The synthesis of new chiral nicotinamide adenine dinucleotide hydrogenated models derived from quinoline is described. Using a biomimetic approach, the out-of-plane positioning of the amide carbonyl was obtained by involving the chiral auxiliary in a lactam structure. It is shown that electron-donating groups on the benzene ring of the quinoline structure are necessary to obtain high chemical yields during the reduction of methyl benzoylformate. An interesting variation of the enantioselectivity as a function of magnesium ion concentration has been observed. Under the best conditions, methyl mandelate was obtained in up to 95% ee (R). To facilitate the recycling of these models, grafting of reagent 4 on a Merrifield resin has been developed. The resulting polymer-supported reagent 4 was tested in the asymmetric reduction of methyl benzoylformate.