SYNTHESIS OF POLYSUBSTITUTED INDOLES AND INDOLINES BY MEANS OF ZIRCONOCENE-STABILIZED BENZYNE COMPLEXES

被引：100

作者：

TIDWELL, JH ^{[1
]}

BUCHWALD, SL ^{[1
]}

机构：

[1] MIT,DEPT CHEM,CAMBRIDGE,MA 02139

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1994年 / 116卷 / 26期

关键词：

D O I：

10.1021/ja00105a021

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The development of a new method for the regiospecific synthesis of polysubstituted indoles and indolines is reported. The key steps involve the generation of zirconocene-stabilized benzyne complexes and subsequent intramolecular olefin insertion reactions to provide tricyclic indoline zirconacycles. The zirconacyclic intermediates were cleaved with iodine to yield diiodo indolines, which were converted to a wide variety of indole and indoline products, such as analogs of tryptamine, serotonin, tryptophan, and the pharmacophore of CC-1065.

引用

页码：11797 / 11810

页数：14

共 119 条

[1] ENE REACTION OF THE ACTIVE IMINO GROUP - A NOVEL SYNTHESIS OF ALPHA-AMINO-ACIDS [J].