Synthesis of symmetrical and unsymmetrical 3,3-di(indolyl)indolin-2-ones under controlled catalysis of ionic liquids

被引：93
作者：
Rad-Moghadam, Kurosh [1 ]
Sharifi-Kiasaraie, Masoumeh [1 ]
Taheri-Amlashi, Homayun [1 ]
机构：
[1] Univ Guilan, Dept Chem, Rasht, Iran
来源：
TETRAHEDRON | 2010年 / 66卷 / 13期
关键词：
Indole; Isatin; Oxindole; Ionic liquid; OXINDOLE ALKALOIDS; KINASE INHIBITORS; INDOLE ALKALOIDS; ISATIN; DERIVATIVES; EFFICIENT; FACILE; ACID; CONDENSATION; KETONES;
D O I：
10.1016/j.tet.2010.02.017
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Three ionic liquids, [BMIM][BF4] doped with 60 mol % of LiCl ([BMIM][BF4]-LiCl), N,N,N,N-tetramethylguanidinium trifluoroacetate (TMGT), and N,N,N,N-tetramethylguanidinium triflate (TMGT(f)) were found useful as catalyst solvents for controlled 3-indolylation of isatins. Our investigation revealed that the reaction between isatin and indoles in [BMIM][BF4]-LiCl or TMGT(f) media stops at the step of addition of the two components providing 3-indolyl-3-hydroxyindolin-2-ones while the ionic liquid TMGT runs the reaction further through accompanying Friedel-Crafts substitution to afford symmetrical 3,3-di(indol-3-yl)indolin-2-ones. To take advantage of the difference between the effects of these ionic liquids on the reaction progress, we planned a two-step protocol for the efficient synthesis of unsymmetrical 3,3-di(indol-3-yl)indolin-2-ones. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码：2316 / 2321
页数：6
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