Heteroarylation of 1-azulenyl methyl sulfide: Two-step synthetic strategy for 1-methylthio-3-(heteroaryl)azulenes using the triflate of N-containing heterocycles

Junya Higashi, Taku Shoji, Shunji Ito, Kozo Toyota, Masafumi Yasunami, Noboru Morita

Research output: Contribution to journalArticlepeer-review

22 Citations (Scopus)

Abstract

1-Azulenyl methyl sulfide reacts with highly electrophilic trifluoromethanesulfonates of N-heterocycles, that is, pyridine, isoquinoline, 1,10-phenanthroline, benzothiazole, quinoline, and acridine, to give 1-methylthio-3-(dihydroheteroaryl)azulenes in good yields. In the case of the reaction with the trifluoromethanesulfonate of pyridine, 1-methylthio-3- pyridylazulene was obtained directly under certain reaction conditions. Treatment of the 1-methylthio-3-(dihydroheteroaryl)-azulenes with KOH or tBuOK afforded the corresponding 1-methylthio-3-(heteroaryl)azulenes in good yields. The redox behavior of these 1-methylthio-3-(heteroaryl)azulenes was examined by cyclic voltammetry and differential pulse voltammetry.

Original languageEnglish
Pages (from-to)5823-5831
Number of pages9
JournalEuropean Journal of Organic Chemistry
Issue number34
DOIs
Publication statusPublished - 2008 Dec 1

Keywords

  • Azulene
  • Electrochemistry
  • Electrophilic substitution
  • Heteroarylation

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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