Synthesis of 5-substituted indole derivatives, Part 5. A synthesis of 5-formyl-1H-indole-2-carboxylates: The CH2SO3H functionality as a masked formyl group

New synthetic intermediates, ethyl 5-formyl-1H-indole-2-carboxylates (4) were prepared from 2-ethoxycarbonyl-IH-indole-5-methanesulfonic acids (1). The transformation of the sulfomethyl group to formyl function was accomplished through elimination of SO2 to yield ethyl 5-chloromethyl-1H-indole-2-car...

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Bibliographic Details
Published inHeterocycles Vol. 60; no. 12; pp. 2761 - 2766
Main Authors Pete, B, Parlagh, G, Tole, L
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 01.12.2003
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
5-chloromethylindole
oxidation
5-hydroxymethylindole
5-formylindole
indole-5-methanesulfonic acid
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Summary:New synthetic intermediates, ethyl 5-formyl-1H-indole-2-carboxylates (4) were prepared from 2-ethoxycarbonyl-IH-indole-5-methanesulfonic acids (1). The transformation of the sulfomethyl group to formyl function was accomplished through elimination of SO2 to yield ethyl 5-chloromethyl-1H-indole-2-carboxylates (2), hydrolysed to ethyl 5-hydroxymethyl-1H-indole-2-carboxylates (3), then oxidized to aldehydes (4).
ISSN:0385-5414
DOI:10.3987/COM-03-9879