7697-69-0Relevant academic research and scientific papers
Iodine-catalyzed sulfuration of isoquinolin-1(2H)-ones applying ethyl sulfinates
Mu, Yangxiu,Yang, Minghua,Li, Fengxia,Iqbal, Zafar,Jiang, Rui,Hou, Jing,Guo, Xin,Yang, Zhixiang,Tang, Dong
supporting information, p. 4934 - 4937 (2021/03/26)
An efficient sulfuration of isoquinolin-1(2H)-ones at the C-4 position is reported by employing ethyl sulfinates, and the corresponding products are obtained in moderate to excellent yields in the presence of iodine. This synthetic strategy provides a range of thioether-isoquinolin-1(2H)-ones while tolerating a number of functional groups on the isoquinoline nitrogen atom and benzene ring. In addition, pyridin-2(1H)-one is also reacted smoothly and afforded the corresponding thioether product in moderate yield. A plausible mechanism is suggested based on the preliminary mechanistic studies.
Integrating Allyl Electrophiles into Nickel-Catalyzed Conjunctive Cross-Coupling
Derosa, Joseph,Engle, Keary M.,Gallagher, Timothy J.,Li, Zi-Qi,Liu, Peng,Tran, Van T.
supporting information, p. 7029 - 7034 (2020/03/23)
Allylation and conjunctive cross-coupling represent two useful, yet largely distinct, reactivity paradigms in catalysis. The union of these two processes would offer exciting possibilities in organic synthesis but remains largely unknown. Herein, we repor
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.
Carbene-catalyzed aerobic oxidation of isoquinolinium salts: Efficient synthesis of isoquinolinones
Wang, Guanjie,Hu, Wanyao,Hu, Zhouli,Zhang, Yuxia,Yao, Wei,Li, Lin,Fu, Zhenqian,Huang, Wei
, p. 3302 - 3307 (2018/07/29)
A mild and environmentally friendly carbene-catalyzed aerobic oxidation of isoquinolinium salts was successfully realized. Accordingly, a diverse set of isoquinolinones and phenanthridinones was efficiently prepared in good to excellent yields. The mechanistic study indicates that the formation of an aza-Breslow intermediate is the crucial step in this transformation. This reaction features ambient air as the sole oxidant and oxygen source, a broad substrate scope, and excellent functional-group tolerance and proceeds under mild reaction conditions. Furthermore, a highly efficient synthesis of bioactive molecules and natural products including N-methylcrinasiadine, N-isopentylcrinasiadine, N-phenethylcrinasiadine, isoindolo[2,1-b]isoquinolin-5(7H)-one, PJ-34, rac-Gusanlung D, rosettacin, 8-oxopseudopalmatine and ilicifoline B was accomplished.
An organocatalyst bound α-aminoalkyl radical intermediate for controlled aerobic oxidation of iminium ions
Motaleb, Abdul,Bera, Asish,Maity, Pradip
supporting information, p. 5081 - 5085 (2018/07/29)
A catalyst bound α-aminoalkyl radical intermediate from iminium is developed to control its formation and reactivity with aerobic oxygen. The influence of the catalyst was demonstrated via the ease of radical intermediate formation and its subsequent reactivity, including the first catalyst-controlled enantioselective aerobic oxidation with a chiral phosphite catalyst.
