A New Method for the Preparation of 2-Alkoxybenzoxazoles

Masatoshi Yamato, Yasuo Takeuchi, Kyoko Hattori, Kuniko Hashigaki

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

A one-pot synthesis of 2-alkoxybenzoxazole (I) from benzoxazoline-2-thione (II) was achieved. Treatment of benzoxazoline-2-thione with methyl iodide followed by an alcohol at room temperature in the presence of sodium hydride gave I. The reaction involves the intermediate of 2-(methylthio)benzoxazole (IIIa), followed by substitution of the methylthio group by an alkoxide anion. The general applicability of this method is discussed.

Original languageEnglish
Pages (from-to)3946-3950
Number of pages5
JournalChemical and Pharmaceutical Bulletin
Volume31
Issue number11
DOIs
Publication statusPublished - Aug 1983

Keywords

  • 2-(alkylthio)benzoxazole
  • 2-(dialkoxymethylene)aminophenol
  • 2-alkoxybenzoxazole
  • 4-tert-butylcyclohexanol
  • benzoxazoline-2-thione

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

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