Synthesis of 3-substituted indazoles and benzoisoxazoles via Pd-catalyzed cyclization reactions: application to the synthesis of nigellicine

Kiyofumi Inamoto, Mika Katsuno, Takashi Yoshino, Yukari Arai, Kou Hiroya, Takao Sakamoto

Research output: Contribution to journalArticlepeer-review

84 Citations (Scopus)

Abstract

Syntheses of 3-substituted indazoles and benzoisoxazoles were efficiently accomplished with the aid of Pd-catalyzed intramolecular carbon-nitrogen and carbon-oxygen bond formations. The catalyst system described herein allows the cyclization to proceed under very mild conditions and thus could be applied to a wide range of substrates with acid- or base-sensitive functional groups. A total synthesis for the indazole ring-containing natural product nigellicine is also described.

Original languageEnglish
Pages (from-to)2695-2711
Number of pages17
JournalTetrahedron
Volume63
Issue number12
DOIs
Publication statusPublished - 2007 Mar 19

Keywords

  • Amination
  • Benzoisoxazole
  • Hydrazone
  • Indazole
  • Nigellicine
  • Palladium

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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