Mechanisms of cyclisation of indolo oxime ethers.: Part 2:: Formation of ethyl 6,8-dimethoxypyrazolo[4,5,1-hi]indole-5-carboxylates

被引：5

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 | 2008年 / 64卷 / 14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.2008.01.100

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'-phenyl-4',6'-dimethoxyindol-7'-yl-2-(hydroxyimino)acetates was investigated using (1)H NMR spectroscopy to determine the mechanism of formation of the corresponding ethyl 6,8-dimethoxypyrazolo[4,5,1-hi]indole-5-carboxylates. The electronic requirements of the reaction were determined and used, along with the effect of removing the ester functionality, to determine that the reaction proceeds through a concerted intramolecular substitution. Crown Copyright (c) 2008 Published by Elsevier Ltd. All rights reserved.

引用

页码：3183 / 3189

页数：7

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