A facile synthesis of 4-, 5- and 6-chloromethyl-1H-indole-2-carboxylates: replacement of a sulfonic acid functionality by chlorine

Valuable new synthetic intermediates, 4-, 5- or 6-chloromethyl-1H-indole-2-carboxylates, were prepared by the facile elimination of SO(2) from 2-ethoxycarbonyl-1H-indole-4-, 5- or 6-methanesulfonic acids, respectively, easily accessible by Fischer-type indolization. (C) 2004 Elsevier Ltd. All rights...

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Bibliographic Details
Published inTetrahedron Vol. 60; no. 40; pp. 8829 - 8837
Main Authors Pete, B, Parlagh, G
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 27.09.2004
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
Japp-Klingemann reaction
FRIEDEL-CRAFTS ACYLATION
Fischer synthesis
5-HT1D RECEPTOR AGONIST
5-SUBSTITUTED INDOLE-DERIVATIVES
6-(chloromethyl)indoles
desulfination
SULFUR
ANTAGONISTS
4-(chloromethyl)indoles
5-(chloromethyl)indoles
CYCLIZATION
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Summary:Valuable new synthetic intermediates, 4-, 5- or 6-chloromethyl-1H-indole-2-carboxylates, were prepared by the facile elimination of SO(2) from 2-ethoxycarbonyl-1H-indole-4-, 5- or 6-methanesulfonic acids, respectively, easily accessible by Fischer-type indolization. (C) 2004 Elsevier Ltd. All rights reserved.
ISSN:0040-4020
DOI:10.1016/j.tet.2004.07.038