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 compound through oxidation and reduction integration (by machine translation)
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Paragraph 9-10, (2020/02/17)
The method takes the aromatic nitro compound and the fatty alcohol as. the raw material and uses the aromatic nitro compound and the fatty, alcohol as the catalyst to, react under an inert atmosphere or under the, 150-200 °C atmosphere containing oxygen 2-12h, at the atmosphere, of oxygen containing, oxygen, to obtain the substituted, quinoline compound, and. the synthesis method can have important application in the aspect of quinoline compound. synthesis. (by machine translation)