One-pot synthesis of tryptanthrin by the Dakin oxidation of indole-3-carbaldehyde

Takumi Abe, Tomoki Itoh, Tominari Choshi, Satoshi Hibino, Minoru Ishikura

Research output: Contribution to journalArticlepeer-review

31 Citations (Scopus)

Abstract

A one-pot approach to indolo[2,1-b]quinazolines from indole-3-carbaldehydes through the Dakin oxidation was developed. It was shown that the reaction proceeded through the condensation of indole-3-carbaldehydes with isatoic anhydrides, derived in situ from indole-3-carbaldehydes by the Dakin oxidation, and further oxidation/cyclization steps.

Original languageEnglish
Pages (from-to)5268-5270
Number of pages3
JournalTetrahedron Letters
Volume55
Issue number38
DOIs
Publication statusPublished - Sep 17 2014
Externally publishedYes

Keywords

  • Dakin oxidation
  • Indole-3-carbaldehyde
  • Indolo[2,1-b]quinazoline
  • Oxidative coupling
  • Urea hydrogen peroxide

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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