Brønsted Acid-Mediated Cycloaromatization of 1H-Indol-2-yl Propargyl Benzoates to 7H-Benzo[c]carbazoles

Javey Khiapeng Tan, Mitch Mathiew, Sanatan Nayak, Philip Wai Hong Chan

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7 Citations (Scopus)

Abstract

A synthetic method for the efficient assembly of benzo[c]carbazole derivatives that relies on silica gel-activated benzoic acid-mediated cycloaromatization of 1H-indol-2-yl propargyl benzoates under atmospheric conditions is described. Robust with a variety of substitution patterns tolerated, the reaction provides a one-step strategy to construct a member of the N-heterocycles family in good to excellent yields. A tentative mechanism is proposed in which the cycloaromatization process is thought to involve a Brønsted acid-mediated formal 1,3-acyloxy migration/6π-electrocyclization pathway.

Original languageEnglish
Pages (from-to)1475-1479
Number of pages5
JournalChemistry - An Asian Journal
Volume12
Issue number13
DOIs
Publication statusPublished - 4 Jul 2017

Keywords

  • alkynes
  • Brønsted acid
  • homogeneous catalysis
  • nitrogen heterocycles
  • silica gel

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