97617-21-5Relevant academic research and scientific papers
Light-driven selective aerobic oxidation of (iso)quinoliniums and related heterocycles
Zhou, Meimei,Yu, Keyang,Liu, Jianxin,Shi, Weimei,Pan, Yingming,Tang, Haitao,Peng, Xiangjun,Liu, Qian,Wang, Hengshan
, p. 16246 - 16251 (2021/05/19)
Selective C1-H/C4-H carbonylation of N-methylene iminium salts, catalyzed by visible-light photoredox and oxygen in the air, has been reported. A ruthenium complex acts as a chemical switch to conduct two different reaction pathways and to afford two diff
Base-promoted aerobic oxidation of: N -alkyl iminium salts derived from isoquinolines and related heterocycles
Bai, Li-Gang,Zhou, Yue,Zhuang, Xin,Zhang, Liang,Xue, Jian,Lin, Xiao-Long,Cai, Tian,Luo, Qun-Li
supporting information, p. 197 - 203 (2020/01/13)
Potassium tert-butoxide-promoted aerobic oxidation of N-alkyl iminium salts is reported. The reaction is atom-economical and environmentally friendly. Iminium salts derived from isoquinoline, quinoline, phenanthridine, phenanthroline, and phthalazine were successfully transformed into their corresponding unsaturated lactams with up to 95% yield under mild conditions in the absence of photocatalysts and metallic or organic catalysts. Owing to the general substrate scope, low cost, feasibility of scale up, wide availability of reagents, and green reaction conditions, this method shows great potential for preparing isoquinolones and related compounds. The method was applied for atom- and step-economical total synthesis of natural products such as norketoyobyrine.
Iodine-Catalyzed Oxidative Functionalization of Azaarenes with Benzylic C(sp3)-H Bonds via N-Alkylation/Amidation Cascade: Two-Step Synthesis of Isoindolo[2,1-b]isoquinolin-7(5H)-one
Luo, Wen-Kun,Shi, Xin,Zhou, Wang,Yang, Luo
supporting information, p. 2036 - 2039 (2016/06/01)
An efficient and practical iodine-catalyzed oxidative functionalization of azaarenes with benzylic C-H bonds via an N-alkylation and amidation cascade is developed to provide isoquinolin-1(2H)-ones. This method utilizes readily available unfunctionalized azaarenes and methylarenes as starting materials and proceeds under metal-free conditions with good to excellent yields, avoiding the use of expensive noble metal catalysts and generation of halide and metal wastes. The synthetic utility of this reaction is exemplified by the concise, two-step synthesis of isoindolo[2,1-b]isoquinolin-7(5H)-one.
Ruthenium-Mediated Dual Catalytic Reactions of Isoquinoline via C?H Activation and Dearomatization for Isoquinolone
Wang, Ting-Hsuan,Lee, Wei-Chih,Ong, Tiow-Gan
supporting information, p. 2751 - 2758 (2016/09/13)
We have unraveled the ruthenium-promoted prototype reaction based on C(sp2)?C(sp3) bond formation through the reigoselective C?H activation of isoquinoline and pyridine derivatives with various alkyl halides, leading to 1-substituted isoquinoline products in good yield. This C?H catalytic reaction did not rely on chelation assistance of the directing group of the substrates. The dimer [RuCl2(p-cymene)]2in combination with an N-heterocyclic carbene ligand, adamantanecarboxylic acid and K2CO3base in N-methyl-2-pyrrolidone solution at 150 °C are the best conditions. Simultaneously, we are also able to chemically tune the reaction mode to dearomatization by adding water, leading to isoquinolone products. This reaction methodology is not suitable for other nitrogen-containing heteroarenes such as pyridazines and pyrimidines. (Figure presented.).
