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

Alexey Kuznetsov, Anton Makarov, Aleksandr E. Rubtsov, Alexander V. Butin, Vladimir Gevorgyan

Research output: Contribution to journalArticle

33 Scopus citations

Abstract

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.

Original languageEnglish (US)
Pages (from-to)12144-12153
Number of pages10
JournalJournal of Organic Chemistry
Volume78
Issue number23
DOIs
StatePublished - Dec 6 2013
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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