The novel transition metal free synthesis of 1,1′-biazulene

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

Research output: Contribution to journalArticle

33 Citations (Scopus)

Abstract

Reaction of 1-azulenyl methyl sulfoxide (1) under acidic conditions gave the 1,1′-biazulene derivative 3. Methylmercapt groups of 3 were readily converted to formyl groups by Vilsmeier reaction to afford 3,3′-diformyl-1,1′-biazulene (4), which reacted with pyrrole in the presence of acetic acid to give the parent 1,1′-biazulene (5). Reaction of 5 with pyridine in the presence of Tf2O gave 3,3′-dihydropyridyl-1,1′-biazulene derivative 6. 3,3′-(4-Pyridyl)-1,1′-biazulene (7) was obtained by the reaction of 3 with KOH in EtOH at room temperature in good yield.

Original languageEnglish
Pages (from-to)4999-5002
Number of pages4
JournalTetrahedron Letters
Volume48
Issue number29
DOIs
Publication statusPublished - 2007 Jul 16

Keywords

  • Aryl-aryl coupling
  • Azulene
  • Biazulene
  • Pyridinylation

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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