BiCl3-Mediated Tandem Cyclization of Tryptamine-Derived Ynamide: Concise Synthesis of Pentacyclic Spiroindolines and Tricyclic Indole Derivatives

Lin，Xiao Tong1; Zhao，Cheng1; Wang，Da Ru1; Wu，Guang Cheng1; Chen，Guo Shu1; Chen，Shu Jie1; Ren，Hai2; Deng，Dong Sheng4; Xu，Yi Bing1; Hu，Xiao Wei1; Liu，Yun Lin1,2,3

2022-02-15

10.1002/adsc.202101232

ADVANCED SYNTHESIS & CATALYSIS   影响因子和分区

1615-4150

1615-4169

Catalytic tandem cyclization of ynamides has attracted considerable interest in organic synthesis because of its atom economy in the rapid formation of polycyclic compounds. However, examples on the construction of pentacyclic spiroindolines are quite scarce. Herein, we described a BiCl-mediated tandem cyclization reaction of tryptamine-ynamides, which led to the formation of appealing pentacyclic spiroindoline scaffolds in moderate to excellent yields. In addition, such a reaction can lead to the divergent synthesis of tricyclic indole derivatives with moderate yields by engineering substrate structures. The synthetic utility of this methodology has also been demonstrated by further interesting transformations. (Figure presented.).

bismuth catalysis pentacyclic spiroindoline tandem cyclization tricyclic indole derivative tryptamine-derived ynamide

SCI ; IC ; CCR

英语

其他

Guangzhou Municipal Science and Technology Project[202102020784];Natural Science Foundation of Guangdong Province[2021A1515010072];State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Medical University[QJHKY2022389];

WOS:000735418800001

2-s2.0-85122109259

Scopus

1.School of Chemistry and Chemical Engineering,Guangzhou University,Guangzhou,230 Wai Huan Xi Road, Guangzhou Higher Education Mega Center,510006,China
2.State Key Laboratory of Functions and Applications of Medicinal Plants,Guizhou Medical University,Guiyang,550014,China
3.Guangdong Provincial Key Laboratory of Catalysis,Southern University of Science and Technology,Shenzhen,518055,China
4.College of Chemistry and Chemical Engineering,Luoyang Normal University,Luoyang,471934,China

Lin，Xiao Tong,Zhao，Cheng,Wang，Da Ru,et al. BiCl3-Mediated Tandem Cyclization of Tryptamine-Derived Ynamide: Concise Synthesis of Pentacyclic Spiroindolines and Tricyclic Indole Derivatives[J]. ADVANCED SYNTHESIS & CATALYSIS,2022,364(4):890-896.

Lin，Xiao Tong.,Zhao，Cheng.,Wang，Da Ru.,Wu，Guang Cheng.,Chen，Guo Shu.,...&Liu，Yun Lin.(2022).BiCl3-Mediated Tandem Cyclization of Tryptamine-Derived Ynamide: Concise Synthesis of Pentacyclic Spiroindolines and Tricyclic Indole Derivatives.ADVANCED SYNTHESIS & CATALYSIS,364(4),890-896.

Lin，Xiao Tong,et al."BiCl3-Mediated Tandem Cyclization of Tryptamine-Derived Ynamide: Concise Synthesis of Pentacyclic Spiroindolines and Tricyclic Indole Derivatives".ADVANCED SYNTHESIS & CATALYSIS 364.4(2022):890-896.