Synthesis of the benzo-β-carboline isoneocryptolepine: The missing indoloquinoline isomer in the alkaloid series cryptolepine, neocryptolepine and isocryptolepine

Steven Hostyn, Bert U.W. Maes, Luc Pieters, Guy L.F. Lemière, Péter Mátyus, György Hajós, Roger A. Dommisse

Research output: Contribution to journalArticle

74 Citations (Scopus)

Abstract

7H-Indolo[2,3-c]quinoline has been synthesized in two steps via a new approach starting from commercially available 3-bromoquinoline and 2-bromoaniline. The new methodology consists of two consecutive palladium-catalyzed reactions: a selective Buchwald/Hartwig amination followed by an intramolecular Heck-type reaction. Alternatively, the same skeleton has also been prepared via the combination of a Suzuki arylation with an intramolecular nitrene insertion starting from 4-chloroquinoline and {2-[(2,2-dimethylpropanoyl)amino]phenyl}boronic acid. Selective methylation of 7H-indolo[2,3-c]quinoline yielded 5-methyl-5H-indolo[2,3-c]quinoline (Isoneocryptolepine) which is an interesting new lead compound in the search for new antiplasmodial drugs.

Original languageEnglish
Pages (from-to)1571-1577
Number of pages7
JournalTetrahedron
Volume61
Issue number6
DOIs
Publication statusPublished - Feb 7 2005

Keywords

  • Amination
  • Heck-type reaction
  • Malaria
  • Nitrene insertion
  • Palladium
  • Suzuki

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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