Synthesis of heterocyclic compounds through palladium-catalyzed C-H cyclization processes

Kiyofumi Inamoto

Research output: Contribution to journalReview articlepeer-review

15 Citations (Scopus)

Abstract

Herein, we describe our development of synthetic methods for heterocyclic compounds based on the palladium-catalyzed carbon-hydrogen bond (C-H) functionalization/intramolecular carbon-heteroatom (nitrogen or sulfur) bond formation process. By this C-H cyclization method, we efficiently prepared various N-heterocycles, including indazoles, indoles, and 2-quinolinones, as well as S-heterocycles such as benzothiazoles and benzo[b]thiophenes. Yields are typically good to high and good functional-group tolerance is observed for each process, thereby indicating that the method provides a novel, highly applicable synthetic route to the abovementioned biologically important heterocyclic frameworks. As an application of this approach, an auto-tandem-type, one-pot process involving the oxidative Heck reaction and subsequent C-H cyclization using cinnamamides and arylboronic acids as starting materials in the presence of a palladium catalyst was also developed for the rapid construction of the 2-quinolinone nucleus.

Original languageEnglish
Pages (from-to)987-996
Number of pages10
JournalChemical and Pharmaceutical Bulletin
Volume61
Issue number10
DOIs
Publication statusPublished - 2013 Oct

Keywords

  • C-H functionalization
  • Cyclization
  • Heterocyclic compound
  • Palladium

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

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