Divergent synthesis of 6H-isoindolo[2,1-a]indol-6-ones and indenoindolones: an investigation of Pd-catalyzed isocyanide insertion |
| |
Authors: | Ting Tang Xiao JiangJin-Mei Wang Yin-Xing SunYong-Ming Zhu |
| |
Institution: | College of Pharmaceutical Sciences, Soochow University, Suzhou 215123, China |
| |
Abstract: | A novel Pd-catalyzed intramolecular cyclization via tert-butyl isocyanide insertion from 2-(2-bromophenyl)-1H-indoles has been developed, which demonstrates the utility of isocyanides in C–N or C–C bond construction. Treatment of 2-(2-bromophenyl)-1H-indoles with tert-butyl isocyanide affords 6H-isoindolo2,1-a]indol-6-ones with high efficiency. However, N-methyl or N-Boc protected 2-(2-bromophenyl)-1H-indoles gives indenoindolones in excellent yields under the same condition, which reveals that under the described situation, isocyanides insertion for the formation of C–N bonds is prior to that of C–C bonds. |
| |
Keywords: | Isocyanides Palladium C&ndash N and C&ndash C bonds Synthetic methods Nitrogen heterocycles |
本文献已被 ScienceDirect 等数据库收录! |
|