Base-induced cyclisation of ortho-substituted 2-phenyloxazolines to give 3-aminobenzofurans and related heterocycles

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Abstract

Treatment of ortho-benzyloxyphenyloxazolines with butyllithium and potassium t-butoxide results in cyclisation with ring-opening of the oxazoline to give 2-aryl-3-aminobenzofurans. The reaction also occurs with the corresponding benzylthio- and benzylamino-compounds to give benzothiophenes and indoles, respectively. Use of an ortho-allyloxyphenyloxazoline gives the corresponding 2-vinylbenzofuran, while both α-methylbenzyloxy and benzylsulfonyl compounds form stable spirooxazolidine products. The X-ray structure of an aminobenzothiophene product has been determined.
Original languageEnglish
Pages (from-to)1738-1742
Number of pages5
JournalSynlett
Volume28
Issue number14
Early online date18 Jul 2017
DOIs
Publication statusPublished - 18 Aug 2017

Keywords

  • Cyclisation
  • Oxazoline
  • Benzofuran
  • Benzothiophenes
  • Indole
  • Schlosser’s base
  • Spiro heterocycle

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