Mechanisms of cyclisation of indolo oxime ethers I.: Formation of ethyl 9,11-dimethoxy indolo[2,3-c]quinoline-6-carboxylates

被引：13

作者：

Clayton, Kylie A. ^{[1
]}

Black, David Stc. ^{[1
]}

Harper, Jason B. ^{[1
]}

机构：

[1] Univ New S Wales, Sch Chem, Sydney, NSW 2052, Australia

来源：

TETRAHEDRON | 2007年 / 63卷 / 43期

基金：

澳大利亚研究理事会;

关键词：

indole; cyclisation; mechanism determination;

D O I：

10.1016/j.tet.2007.08.026

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The cyclisation of a series of ethyl 3'-aryl-4',6'-dimethoxyindol-2'-yl-2-(hydroxyimino)acetates was investigated using H-1 NMR spectroscopy to determine the mechanism of formation of the corresponding ethyl 9,11-dimethoxy indolo[2,3-c] quinoline-6-carboxylates. The electronic requirements of the reaction were determined and, along with the observation of an intermediate in the process, indicated that the reaction proceeds through an electrocyclic mechanism. The importance of the ester moiety in such a process is discussed. Crown Copyright (C) 2007 Published by Elsevier Ltd. All rights reserved.

引用

页码：10615 / 10621

页数：7

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