A Short, Novel, and Practical Synthesis of 3-Alkenylated Indoles

Direct metal-free alkenylation of 2-methylindole via acid-mediated Michael addition-elimination reaction with ethoxymethylenemalononitrile or ethyl ethoxymethylenecyanoacetate affords 3-indolyl-2-cyanoacrylonitrile and ethyl 3-indolyl-2-cyanoacrylate. Behavior of 1H-indole is predictably different.

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Bibliographic Details
Published inSynthetic communications Vol. 43; no. 12; pp. 1743 - 1749
Main Authors Kargar, Mojgan, Hekmatshoar, Rahim, Mostashari, Abdol Jalil
Format Journal Article
LanguageEnglish
Published Philadelphia Taylor & Francis Group 18.06.2013
Taylor & Francis Ltd
Subjects
Ethoxymethylenemalononitrile
ethyl ethoxymethylenecyanoacetate
indolealkenylation
Michael addition-elimination
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Summary:Direct metal-free alkenylation of 2-methylindole via acid-mediated Michael addition-elimination reaction with ethoxymethylenemalononitrile or ethyl ethoxymethylenecyanoacetate affords 3-indolyl-2-cyanoacrylonitrile and ethyl 3-indolyl-2-cyanoacrylate. Behavior of 1H-indole is predictably different.
ISSN:0039-7911
1532-2432
DOI:10.1080/00397911.2012.666817