Synthesis of 3-Substituted Benzoxazoline-2-thiones

Masatoshi Yamato, Yasuo Takeuchi, Kuniko Hashigaki, Kyoko Hattori, Eiko Muroga, Takashi Hirota

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5 Citations (Scopus)

Abstract

Several methods for the preparations of 3-substituted benzoxazoline-2-thiones (1) were examined. Method B via the thiation of 3-substituted benzoxazolin-2-one (5) with phosphorus pentasulfide was found to be applicable to the preparation of most analogs of 1, with a few exceptions. Method C via the cyclization of 2-(alkylamino)phenol (7) with potassium O-methyldithiocarbonate was suitable for the preparation of analogs with a group sensitive to high temperature or with an aryl- (including aromatic hetero-cyclic ring) methyl group. In addition, the reaction of benzoxazoline-2-thione (2) with acetals such as 1-ethoxy-isochroman, 2-ethoxytetrahydrofuran, and 2-ethoxytetrahydropyran, or with Michael acceptors such as 2,3-dihydrofuran and 2H-3,4-dihydropyran, gave 3-substituted benzoxazoline-2-thione (1d—f).

Original languageEnglish
Pages (from-to)1733-1737
Number of pages5
JournalChemical and Pharmaceutical Bulletin
Volume31
Issue number5
DOIs
Publication statusPublished - 1983

Keywords

  • 2-(alkylamino) phenol
  • 2-(alkylthio)benzoxazole
  • 3-substituted benzoxazolin-2-one
  • 3-substituted benzoxazoline-2-thione
  • acetal
  • Michael acceptor
  • thiation
  • UV spectra

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

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  • Cite this

    Yamato, M., Takeuchi, Y., Hashigaki, K., Hattori, K., Muroga, E., & Hirota, T. (1983). Synthesis of 3-Substituted Benzoxazoline-2-thiones. Chemical and Pharmaceutical Bulletin, 31(5), 1733-1737. https://doi.org/10.1248/cpb.31.1733