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

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

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Bibliographic Details
Published inTetrahedron Vol. 60; no. 40; pp. 8829 - 8837
Main Authors Pete, Béla, Parlagh, Gyula
Format Journal Article
LanguageEnglish
Published Elsevier Ltd 2004
Subjects
4-(Chloromethyl)indoles
5-(Chloromethyl)indoles
6-(Chloromethyl)indoles
Desulfination
Fischer synthesis
Japp-Klingemann reaction
Japp-Klingemann reaction
Fischer synthesis
5-(Chloromethyl)indoles
6-(Chloromethyl)indoles
4-(Chloromethyl)indoles
Desulfination
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Summary:Valuable new synthetic intermediates, 4-, 5- or 6-chloromethyl-1 H-indole-2-carboxylates, were prepared by the facile elimination of SO 2 from 2-ethoxycarbonyl-1 H-indole-4-, 5- or 6-methanesulfonic acids, respectively, easily accessible by Fischer-type indolization. 4-, 5- and 6-(Chloromethyl)indoles were prepared from indole-4-, 5- and 6-methanesulfonic acids, respectively, by replacement of the sulfo group with chlorine. The indole-methanesulfonic acids were prepared by Fischer synthesis.
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2004.07.038