23023-38-3Relevant academic research and scientific papers
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.
Regioselective Access to 3-Aryl-1-aminoisoquinolines via Nickel(I)-Catalyzed C-C and C-N Cascade Coupling Reactions from the Substituted 2-(Cyanomethyl)benzonitriles
Yang, Xicheng,Yu, Haihua,Xu, Yulong,Shao, Liming
, p. 9682 - 9695 (2018/09/06)
A novel and regioselective Ni(I) catalyzed C-C and C-N cascade coupling reactions has been developed. The cascade furnishes atom-economic access to 40 3-aryl-1-aminoisoquinolines. The regioselectivity of C(sp3)-cyano group over C(sp2
Potassium tert-Butoxide-Promoted Synthesis of 1-Aminoisoquinolines from 2-Methylbenzonitriles and Benzonitriles under Catalyst-Free Conditions
Feng, Jian-Bo,Wu, Xiao-Feng
supporting information, p. 2179 - 2185 (2016/07/16)
Herein a practical and efficient protocol for preparing a range of aminoisoquinolines is reported. Various aminoisoquinolines were prepared in moderate to good yields from the corresponding 2-methylbenzonitriles and benzonitriles upon treatment with potas
Modification of 3-arylisoquinolines into 3,4-diarylisoquinolines and assessment of their cytotoxicity and topoisomerase inhibition
Khadka, Daulat Bikram,Woo, Hyunjung,Yang, Su Hui,Zhao, Chao,Jin, Yifeng,Le, Thanh Nguyen,Kwon, Youngjoo,Cho, Won-Jea
, p. 583 - 607 (2015/03/05)
Inspired by the initial success of the monoarylisoquinolines and the quest to identify more potent and selective anticancer agents with topoisomerase (topo) inhibitory activity, series of diarylisoquinolines (3,4-diarylisoquinolones and 3,4-diarylisoquino
Effect of the aryl group substituent in the dimerization of 3-arylisoxazoles to syn 2,6-diaryl-3,7-diazatricyclo[4.2.0.02,5]octan-4,8-diones induced by LDA
Di Nunno, Leonardo,Vitale, Paola,Scilimati, Antonio
experimental part, p. 11198 - 11204 (2009/04/11)
3-Arylisoxazoles react with LDA in THF at 0 °C affording syn-2,6-diaryl-3,7-diazatricyclo[4.2.0.02,5]octan-4,8-diones (bis-azetidinones), via stereoselective dimerization of an azetinone anion intermediate. A?fragmentation reaction affording arylnitriles may compete with electronic and steric effects of the substituent present in the aryl group being pivotal in determining the outcome of this reaction. An interesting behaviour with LDA of arylnitriles arising from the fragmentation reaction of some 3-arylisoxazoles was also observed. N,N-Diisopropylaminobenzonitriles were in fact formed (plausibly via a benzyne mechanism) from 3-(4-chlorophenyl)isoxazole and 3-(2-chlorophenyl)isoxazole, whereas 3-(2-methylphenyl)isoquinolin-1-amine was isolated starting from 3-(2-methylphenyl)isoxazole and LDA.
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.
Molecular modeling of 3-arylisoquinoline antitumor agents active against A-549. A comparative molecular field analysis study
Cho, Won-Jea,Kim, Eui-Ki,Park, Il Yeong,Jeong, Eun Young,Kim, Tae Sung,Le, Thanh Nguyen,Kim, Dae-Duk,Lee, Eung-Seok
, p. 2953 - 2961 (2007/10/03)
A series of 58 3-arylisoquinoline antitumor agents were investigated for defining the pharmacophore model using comparative molecular field analysis (CoMFA) program. The studied compounds related to bioisostere of benzophenanthridine alkaloid were synthes
