Divergent synthesis of 6H-isoindolo[2,1-a]indol-6-ones and indenoindolones: an investigation of Pd-catalyzed isocyanide insertion

作者：Tang, Ting; Jiang, Xiao; Wang, Jin-Mei; Sun, Yin-Xing; Zhu, Yong-Ming^*

来源：Tetrahedron, 2014, 70(18): 2999-3004.

DOI：10.1016/j.tet.2014.03.018

• Isocyanides
• Palladium
• C-N and C-C bonds
• Synthetic methods
• Nitrogen heterocycles

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-isoindolo[2,1-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.

• 出版日期2014-5-6
• 单位苏州大学