Brönsted acid-catalyzed one-pot synthesis of indoles from o-aminobenzyl alcohols and furans

Brönsted acid-catalyzed one-pot synthesis of indoles from o-aminobenzyl alcohols and furans has been developed. This method operates via the in situ formation of aminobenzylfuran, followed by its recyclization into the indole core. The method proved to be efficient for substrates possessing differen...

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Bibliographic Details
Published in:Journal of organic chemistry 2013-12, Vol.78 (23), p.12144-12153
Main Authors: Kuznetsov, Alexey, Makarov, Anton, Rubtsov, Aleksandr E, Butin, Alexander V, Gevorgyan, Vladimir
Format: Article
Language:English
Subjects:
Acids - chemistry
Benzyl Alcohols - chemistry
Furans - chemistry
Indoles - chemical synthesis
Indoles - chemistry
Molecular Structure
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Summary:Brönsted acid-catalyzed one-pot synthesis of indoles from o-aminobenzyl alcohols and furans has been developed. This method operates via the in situ formation of aminobenzylfuran, followed by its recyclization into the indole core. The method proved to be efficient for substrates possessing different functional groups, including -OMe, -CO2Cy, and -Br. The resulting indoles can easily be transformed into diverse scaffolds, including 2,3- and 1,2-fused indoles, and indoles possessing an α,β-unsaturated ketone moiety at the C-2 position.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo402132p