Synthesis of Dihydrobenzisoxazoles by the [3+2] Cycloaddition of Arynes and Oxaziridines
JOURNAL OF ORGANIC CHEMISTRY, cilt.75, sa.21, ss.7381-7387, 2010 (SCI-Expanded, Scopus)
- 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.