On-Water Silver(I)-Catalyzed Cycloisomerization of Acetylenic Free Amines/Amides towards 7-Azaindole/Indole/Isoquinolone Derivatives

被引：15

作者：

Sun, Hongpeng ^{[1
]}

Xiao, Li ^{[1
]}

Li, Wei ^{[1
,2
]}

Xie, Qiong ^{[1
,2
]}

Shao, Liming ^{[1
,2
]}

机构：

[1] Fudan Univ, Sch Pharm, 826 Zhangheng Rd,Zhangjiang Hitech Pk, Shanghai 201203, Peoples R China

[2] Shanghai Ctr Drug Discovery & Dev, 826 Zhangheng Rd,Zhangjiang Hitech Pk, Shanghai 201203, Peoples R China

来源：

SYNTHESIS-STUTTGART | 2017年 / 49卷 / 21期

关键词：

on-water; cycloisomerization; 7-azaindoles; indoles; isoquinolones; REMARKABLE CATALYTIC-ACTIVITY; MICROWAVE-ASSISTED SYNTHESIS; INDOLE-DERIVATIVES; STEREOSELECTIVE-SYNTHESIS; 2-ALKYNYLANILINES; HETEROCYCLES; INHIBITORS; 7-AZAINDOLES; REACTIVITY; POTASSIUM;

D O I：

10.1055/s-0036-1589072

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Silver-catalyzed on-water intramolecular cyclization of acetylenic free amines is reported, which affords 7-azaindoles in good to excellent yields. Neither strong base/acid catalysts nor N-substituted substrates are required to achieve this cycloisomerization. Hydrogen bonds between water medium and the substrates play an important role in improving chemical reactivity and regioselectivity. Furthermore, the on-water reaction is extendable to acetylenic amides for isoquinolone synthesis.

引用

页码：4845 / 4852

页数：8