A New Method for the Preparation of 2-(Alkylamino)benzoxazoles and 2-(Alkylimino)benzoxazolines

Masatoshi Yamato, Yasuo Takeuchi, Kyoko Hattori, Kuniko Hashigaki

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

New syntheses of 2-(alkylamino)benzoxazoles (III) and 3-alkyI-2-(alkylimino)benzoxazolines (IV) were developed. Various compounds III were obtained by the reactions of 2-(methylthio)benzoxazole with amines. In the alkylation of 2-(monoalkylamino)benzoxazoles, the use of a base as a catalyst was found to be important for the selective preparation of 2-(N, N-dialkylamino)benzoxazoles; in the absence of base, IV was obtained. On the other hand, alkylation of N, N ′-dialkyl-N-(2-hydroxyphenyl)thioureas resulted in the development of another method for the preparation of IV.

Original languageEnglish
Pages (from-to)3053-3060
Number of pages8
JournalChemical and Pharmaceutical Bulletin
Volume32
Issue number8
DOIs
Publication statusPublished - 1984

Keywords

  • 2-(alkylamino)benzoxazole
  • 2-(methylthio)benzoxazole
  • 3-alkyl-2-(alkylimino)benzoxazoline
  • 3-alkylbenzoxazoline-2-thione
  • N, N'-dialkyl-N-(2-hydroxyphenyl)thiourea

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

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