Synthesis of dihydrobenzisoxazoles by the [3 + 2] cycloaddition of arynes and oxaziridines

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KIVRAK A., Larock R. C.

Journal of Organic Chemistry, vol.75, no.21, pp.7381-7387, 2010 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 75 Issue: 21
  • Publication Date: 2010
  • Doi Number: 10.1021/jo101656c
  • Journal Name: Journal of Organic Chemistry
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.7381-7387
  • Middle East Technical University Affiliated: No

Abstract

Dihydrobenzisoxazoles are readily prepared in good yields by the [3 + 2] cycloaddition of oxaziridines and arynes. The reaction involves an unusual cleavage of the C-O bond of the oxaziridine and tolerates a variety of substituents on the oxaziridine and the o-(trimethylsilyl)aryl triflate to form aryl-, heteroaryl-, alkyl-, and naphthyl-substituted dihydrobenzisoxazoles. The resulting halogen-substituted dihydrobenzisoxazoles are readily elaborated to more complex products using palladium-catalyzed crossing-coupling processes. © 2010 American Chemical Society.