Synthesis of Azocino[5,4-b]indoles via Gold-Catalyzed Intramolecular Alkyne Hydroarylation

被引：72

作者：

Peshkov, Vsevolod A. ^{[1
]}

Pereshivko, Olga P. ^{[1
]}

Van der Eycken, Erik V. ^{[1
]}

机构：

[1] Univ Leuven KU Leuven, LOMAC, Dept Chem, B-3001 Louvain, Belgium

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2012年 / 354卷 / 14-15期

关键词：

C?C coupling; cyclization; gold catalysis; medium-ring compounds; nitrogen heterocycles; INTERMOLECULAR REACTIONS; FUSED HETEROCYCLES; CYCLIZATION; INDOLES; DERIVATIVES; EFFICIENT; REARRANGEMENT; CONSTRUCTION; 1,4-DIYNES; SYSTEMS;

D O I：

10.1002/adsc.201200305

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

An efficient procedure for the synthesis of the azocino[5,4-b]indole framework is presented, relying on a cationic gold-catalyzed intramolecular alkyne hydroarylation of propargylic amides derived from various tryptamines and 3-substituted 2-propynoic acids. The triphenylphosphinegold(I) chloride/silver(I) triflate catalytic system was found to be superior to our previously described mercury(II) triflate catalyst, and hence the substrate scope of the process was significantly expanded.

引用

页码：2841 / 2848

页数：8

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