Azocinoindole Synthesis by a Gold(I)-Catalyzed Ring Expansion of 2-Propargyl-β-Tetrahydrocarboline

被引：32

作者：

Zhang, Lei ^{[1
]}

Chang, Lina ^{[1
]}

Hu, Hongwen ^{[1
]}

Wang, Huaqin ^{[2
]}

Yao, Zhu-Jun ^{[1
]}

Wang, Shaozhong ^{[1
]}

机构：

[1] Nanjing Univ, Sch Chem & Chem Engn, State Key Lab Coordinat Chem, Nanjing 210093, Jiangsu, Peoples R China

[2] Nanjing Univ, Modern Analyt Ctr, Nanjing 210093, Jiangsu, Peoples R China

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2014年 / 20卷 / 10期

基金：

美国国家科学基金会;

关键词：

gold; indoles; reaction mechanisms; ring expansion; X-ray diffraction; SIMPLICISSIMUM ATCC 90288; PENICILLIUM-SIMPLICISSIMUM; OKARAMINE CONGENERS; INDOLE ALKALOIDS; CYCLOPROPYL MOIETY; BETA-CARBOLINES; A-C; GOLD; FRAGMENTATION; ALKYNES;

D O I：

10.1002/chem.201304524

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new methodology taking advantage of gold(I)-catalyzed ring expansion has been developed to assemble tricyclic 1H-azocino[5,4-b]indoles from 2-propargyl--tetrahydrocarbolines. The azocinoindoles were obtained in moderate to excellent yields; the structure of which was established by X-ray crystallographic analysis. A mechanism involving regioselective intramolecular hydroarylation, [1,2]-alkenyl migration and carbon-carbon bond-fragmentation was proposed.

引用

页码：2925 / 2932

页数：8

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