877-43-0Relevant articles and documents
1H, 13C and 15N NMR and GIAO CPHF calculations on two quinoacridinium salts
Jaroszewska-Manaj, Jolanta,Maciejewska, Dorota,Wawer, Iwona
, p. 482 - 485 (2000)
The complete 1H, 13C and 15N NMR assignments of two closely related quinoacridinium salts, 8,13-diethyl-6-methyl-8H-quino[4,3,2-kl]acridinium iodide and, 8,13-diethyl-3,6,11-trimethyl-8H-quino[4,3,2-kl]acridinium iodide, are described. The multinuclear 1D NMR and 2D shift-correlated NMR techniques HMQC, HSQC and HMBC were applied, accompanied by ab initia GIAO CPHF calculations of shielding constants. Copyright
Highly Chemoselective Deoxygenation of N-Heterocyclic N-Oxides Using Hantzsch Esters as Mild Reducing Agents
An, Ju Hyeon,Kim, Kyu Dong,Lee, Jun Hee
supporting information, p. 2876 - 2894 (2021/02/01)
Herein, we disclose a highly chemoselective room-temperature deoxygenation method applicable to various functionalized N-heterocyclic N-oxides via visible light-mediated metallaphotoredox catalysis using Hantzsch esters as the sole stoichiometric reductant. Despite the feasibility of catalyst-free conditions, most of these deoxygenations can be completed within a few minutes using only a tiny amount of a catalyst. This technology also allows for multigram-scale reactions even with an extremely low catalyst loading of 0.01 mol %. The scope of this scalable and operationally convenient protocol encompasses a wide range of functional groups, such as amides, carbamates, esters, ketones, nitrile groups, nitro groups, and halogens, which provide access to the corresponding deoxygenated N-heterocycles in good to excellent yields (an average of an 86.8% yield for a total of 45 examples).
ZnMe2-Mediated, Direct Alkylation of Electron-Deficient N-Heteroarenes with 1,1-Diborylalkanes: Scope and Mechanism
Jo, Woohyun,Baek, Seung-Yeol,Hwang, Chiwon,Heo, Joon,Baik, Mu-Hyun,Cho, Seung Hwan
supporting information, p. 13235 - 13245 (2020/09/01)
The regioselective, direct alkylation of electron-deficient N-heteroarenes is, in principle, a powerful and efficient way of accessing alkylated N-heteroarenes that are important core structures of many biologically active compounds and pharmaceutical agents. Herein, we report a ZnMe2-promoted, direct C2- or C4-selective primary and secondary alkylation of pyridines and quinolines using 1,1-diborylalkanes as alkylation sources. While substituted pyridines and quinolines exclusively afford C2-alkylated products, simple pyridine delivers C4-alkylated pyridine with excellent regioselectivity. The reaction scope is remarkably broad, and a range of C2- or C4-alkylated electron-deficient N-heteroarenes are obtained in good yields. Experimental and computational mechanistic studies imply that ZnMe2 serves not only as an activator of 1,1-diborylalkanes to generate (α-borylalkyl)methylalkoxy zincate, which acts as a Lewis acid to bind to the nitrogen atom of the heterocycles and controls the regioselectivity, but also as an oxidant for rearomatizing the dihydro-N-heteroarene intermediates to release the product.
Method for preparing quinoline derivative
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Paragraph 0037-0038, (2020/02/17)
The invention relates to a method for preparing a quinoline derivative. The method comprises the following steps: by taking aromatic amine compounds and fatty alcohol as raw materials and oxygen-containing molybdenum disulfide as a catalyst, performing a reaction for 2-12 hours in an inert atmosphere or an oxygen-containing atmosphere at the temperature of 120-200 DEG C, after the reaction is finished, separating liquid phase components, performing concentration, and performing separation through a silica gel column, so as to obtain a substituted quinoline compound. The synthetic method may have important application in the aspect of quinoline compound synthesis.
