The nitration of some 4,6-dimethoxyindoles

A range of 3-substituted-4,6-dimethoxyindoles bearing electron-withdrawing groups in either the 2- or 7-position, can be nitrated using nitric acid adsorbed on silica, to give 7-nitro and 2-nitro-indoles, respectively. A 1-cyano-indole gives regioselectively the 2-nitro-indole with loss of the cyano...

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Bibliographic Details
Published in:Tetrahedron 2004-11, Vol.60 (47), p.10779-10786
Main Authors: Jones, Ashley W., Purwono, Bambang, Bowyer, Paul K., Mitchell, Peter S.R., Kumar, Naresh, Nugent, Stephen J., Jolliffe, Katrina A., Black, David StC
Format: Article
Language:English
Subjects:
Indole
Nitration
Nitric acid
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Summary:A range of 3-substituted-4,6-dimethoxyindoles bearing electron-withdrawing groups in either the 2- or 7-position, can be nitrated using nitric acid adsorbed on silica, to give 7-nitro and 2-nitro-indoles, respectively. A 1-cyano-indole gives regioselectively the 2-nitro-indole with loss of the cyano group. Graphical Abstract
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2004.08.086