Stereoselective synthesis of 2,3-disubstituted indoline, pyrrolidine and cyclic ether-fused 1,2-dihydroquinoline derivatives using alkyne iminium ion cyclization of vinylogous carbamates: switch of regioselectivity using an internal hydroxy group as a nucleophile

被引：34

作者：

Gharpure, Santosh J. ^{[1
]}

Prasath, V. ^{[1
]}

Kumar, Vinod ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Bombay 400076, Maharashtra, India

来源：

CHEMICAL COMMUNICATIONS | 2015年 / 51卷 / 71期

关键词：

RADICAL CYCLIZATION; DIASTEREOSELECTIVE SYNTHESIS; CONSTRUCTION; CARBONATES;

D O I：

10.1039/c5cc05292k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An intramolecular, alkyne iminium ion cyclization of vinylogous carbamates derived from o-alkynyl anilines and N-protected homopropargyl amines is developed for the stereoselective construction of trans-2,3-disubstituted indolines and pyrrolidine derivatives, respectively. The regioselectivity of the alkyne iminium ion cyclization could be switched using a hydroxy group as an internal nucleophile resulting in cyclic ether-fused 1,2-dihydroquinolines. The entire process of nitrogen heterocycle formation can also be carried out in a 'one-pot' manner starting from o-iodo aniline derivatives.

引用

页码：13623 / 13626

页数：4