40811-64-1Relevant academic research and scientific papers
Synthesis of (E)-3-Alkylideneindolin-2-ones by an Iron-Catalyzed Aerobic Oxidative Condensation of Csp3–H Bonds of Oxindoles and Benzylamines
Gopalaiah, Kovuru,Tiwari, Ankit
, p. 7229 - 7237 (2020/12/01)
A novel synthetic route for the construction of (E)-3-alkylideneindolin-2-ones through iron-catalyzed aerobic oxidative condensation of oxindoles with benzylamines has been developed. This oxidative reaction involves a sequence of C–H activation, amine self-condensation, nucleophilic addition, and C–C double bond formation. The synthetic importance of this protocol has been demonstrated by preparing tyrosine kinase inhibitors, anticonvulsant and antitumor agents, and other valuable 3-alkylideneindolin-2-one derivatives. Key intermediates are isolated and a plausible mechanistic pathway for the reaction has been discussed.
(E)-3-(Aryl(arylamino)methylene)indolin-2-one derivatives: An efficient synthetic approach and evaluation of their cancer inhibitory activity
Jiang, Hongwu,Feng, Zhiyuan,Chen, Taiping,Li, Zicheng,Huang, Wencai,Luo, Youfu,Zhao, Yinglan
, p. 44 - 49 (2018/02/28)
A series of (E)-3-(aryl(arylamino)methylene)indolin-2-one derivatives were synthesised using an efficient synthetic approach. The method involved reaction of 3-bromo-3-(bromo(aryl)methyl)indolin-2-one with substituted anilines through nucleophilic substitution and a simultaneous elimination using NaHCO3 in DMF. The anticancer activity of the products against four cell lines, HCT-116, A549, SKOV3 and MDA-MB-231, was also evaluated, and several compounds showed moderate inhibitory activity.
Asymmetric catalytic 1,3-dipolar cycloaddition reaction of nitrile imines for the synthesis of chiral spiro-pyrazoline-oxindoles
Wang, Gang,Liu, Xiaohua,Huang, Tianyu,Kuang, Yulong,Lin, Lili,Feng, Xiaoming
supporting information, p. 76 - 79 (2013/04/10)
A new 1,3-dipolar cycloaddition of nitrile imines with 3-alkenyl-oxindoles was catalyzed by a new chiral Mg(ClO4)2 complex of an N,N'-dioxide ligand. The reaction is so far the sole catalytic synthesis of spiro-pyrazoline-oxindole derivatives. A wide variety of substrates were explored to obtain good yields (up to 98%) and excellent enantioselectivities (up to 99%). This cycloaddition expands the scope of propargyl anion type 1,3-dipole in the construction of 2-pyrazoline subunit.
