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

J Org Chem. 2013 Dec 6;78(23):12144-53. doi: 10.1021/jo402132p. Epub 2013 Nov 20.

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.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acids / chemistry*
  • Benzyl Alcohols / chemistry*
  • Furans / chemistry*
  • Indoles / chemical synthesis*
  • Indoles / chemistry
  • Molecular Structure

Substances

  • Acids
  • Benzyl Alcohols
  • Furans
  • Indoles