194292-26-7Relevant academic research and scientific papers
Tandem addition/cyclization for access to isoquinolines and isoquinolones via catalytic carbopalladation of nitriles
Qi, Linjun,Hu, Kun,Yu, Shuling,Zhu, Jianghe,Cheng, Tianxing,Wang, Xiaodong,Chen, Jiuxi,Wu, Huayue
, p. 218 - 221 (2017)
The first example of the palladium-catalyzed sequential nucleophilic addition followed by an intramolecular cyclization of functionalized nitriles with arylboronic acids has been achieved, providing an efficient synthetic pathway to access structurally di
Nickel-Catalyzed Tandem Reaction of Functionalized Arylacetonitriles with Arylboronic Acids in 2-MeTHF: Eco-Friendly Synthesis of Aminoisoquinolines and Isoquinolones
Zhen, Qianqian,Chen, Lepeng,Qi, Linjun,Hu, Kun,Shao, Yinlin,Li, Renhao,Chen, Jiuxi
supporting information, p. 106 - 111 (2019/12/11)
The first example of the nickel-catalyzed tandem addition/cyclization of 2-(cyanomethyl)benzonitriles with arylboronic acids in 2-MeTHF has been developed, which provides the facile synthesis of aminoisoquinolines with good functional group tolerance under mild conditions. This chemistry has also been successfully applied to the synthesis of isoquinolones by the tandem reaction of methyl 2-(cyanomethyl)benzoates with arylboronic acids. The use of the bio-based and green solvent 2-MeTHF as the reaction medium makes the synthesis process environmentally benign. The synthetic utility of this chemistry is also indicated by the synthesis of biologically active molecules.
Synthetic method of antitumor nitrogen-containing heterocyclic drug intermediates
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Paragraph 0044-0049, (2017/07/06)
The invention relates to a synthetic method of isoquinolinone compounds shown by formula (III) shown in the description and acting as antitumor nitrogen-containing heterocyclic drug intermediates; the method comprises: enabling a compound of formula (I) shown in the description and a compound of formula (II) shown in the description to react in a reaction solvent in the presence of a catalyst, a nitrogen-containing ligand and an acid catalyst, and treating after reaction to obtain the compound of formula (III), wherein R1 is C1-C6 alkyl, and R2 is H, halogen, C1-C6 alkyl or C1-C6 alkoxy, or R2 and R2-substituted phenyl form naphthyl. Through the comprehensive selection and interaction of a reaction substrate, catalysts, nitrogen-containing ligands, acid catalysts, reaction solvents and the like according to the method, the substrate range is widened, and the isoquinolinone compound is acquired at high yield; more diversified intermediates are provided for novel synthesis of the compounds and the research, development and synthesis of antitumor drugs, and the compounds have good research value and application potential.
Copper-catalyzed selective synthesis of isoindolin-1-ones and isoquinolin-1-ones from the three-component coupling of 2-halobenzoic acid, alkynylcarboxylic acid and ammonium acetate
Irudayanathan, Francis Mariaraj,Noh, Jieun,Choi, Jinseop,Lee, Sunwoo
, p. 3433 - 3442 (2015/01/09)
Isoindolin-1-ones and isoquinolin-1-ones were selectively synthesized from the reaction of 2-halobenzoic acid, arylalkynylcarboxylic acid and ammonium acetate (NH4OAc) in the presence of cesium carbonate (Cs2CO3) and a copper catalyst. Conducting the reaction under one-pot conditions provided isoindolin-1-ones in good yields. Changing the addition sequence of ammonium acetate after all reagents had reacted at 120 °C for 6 h selectively produced isoquinolin-1-ones. A variety of arylalkynylcarboxylic acids produced the corresponding isoindolin-1-ones and isoquinolin-1-ones in good yields.
Synthesis of functionalized isoquinolin-1(2H)-ones by copper-catalyzed α-arylation of ketones with 2-halobenzamides
Shi, Yan,Zhu, Xuebin,Mao, Haibin,Hu, Hongwen,Zhu, Chengjian,Cheng, Yixiang
supporting information, p. 11553 - 11557 (2013/09/12)
Copper is key: A concise route to isoquinolin-1(2H)-ones from simple and readily available starting materials is provided by an efficient copper-catalyzed annulation of ketones with 2-halobenzamides. The method is applicable to a wide range of ketones con
Synthesis of new 3-arylisoquinolinamines: Effect on topoisomerase I inhibition and cytotoxicity
Cho, Won-Jea,Min, Sun Young,Le, Thanh Nguyen,Kim, Tae Sung
, p. 4451 - 4454 (2007/10/03)
To investigate the structure-activity relationships of 3-arylisoquinolines, diverse substituted 3-aryisoquinolinamines were synthesized and tested in vitro antitumor activity against four tumor cell lines. Some of the compounds showed potent topoisomerase I inhibitory activity. Docking study of 7d with topoisomerase I-DNA complex was also performed.
