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

被引：71
|
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
收藏
页码：2841 / 2848
页数：8
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