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

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 ?,?-unsaturated ketone moiety at the C-2 position.

SUBMITTER: Kuznetsov A

PROVIDER: S-EPMC3923594 | biostudies-literature | 2013 Dec

REPOSITORIES: biostudies-literature

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

Kuznetsov Alexey A Makarov Anton A Rubtsov Aleksandr E AE Butin Alexander V AV Gevorgyan Vladimir V

The Journal of organic chemistry 20131120 23

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-unsatu ...[more]

PMID: 24255969

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