Synthesis of 1-(pyridyl, quinolyl, and isoquinolyl)azulenes by Reissert-Henze type reaction

Taku Shoji, Kazuyuki Okada, Shunji Ito, Kozo Toyota, Noboru Morita

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

Azulene derivatives reacted with N-oxide of several heterocycles in the presence of trifluoromethanesulfonic anhydride (Tf2O) to afford 1-(pyridyl, quinolyl, and isoquinolyl)azulenes in good yield, respectively. In the case of the reaction with the 1-azulenyl methyl sulfide (12), 1,1′-biazulene derivative 13 was obtained under the similar reaction conditions. The first synthesis of unsymmetrical 1,3-di(pyridyl)azulene derivative was also established via our new preparation method following the electrophilic pyridinylation using the reaction with pyridine in the presence of Tf2O.

Original languageEnglish
Pages (from-to)5127-5130
Number of pages4
JournalTetrahedron Letters
Volume51
Issue number39
DOIs
Publication statusPublished - 2010 Sep 29

Keywords

  • Azulene
  • Electrophilic arylation
  • Heterocycle

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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