Synthesis of Dihydrobenzisoxazoles by the [3+2] Cycloaddition of Arynes and Oxaziridines

Kivrak A., Larock R. C.

JOURNAL OF ORGANIC CHEMISTRY, cilt.75, sa.21, ss.7381-7387, 2010 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 75 Sayı: 21
  • Basım Tarihi: 2010
  • Doi Numarası: 10.1021/jo101656c
  • Dergi Adı: JOURNAL OF ORGANIC CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Index Chemicus (IC), Current Chemical Reactions (CCR)
  • Sayfa Sayıları: ss.7381-7387
  • Eskişehir Osmangazi Üniversitesi Adresli: Hayır

Özet

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.