Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 75, Issue 21, Pages 7381-7387Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo101656c
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Funding
- National Institute of General Medical Sciences [GM070620, GM079593]
- National Institutes of Health Kansas University Center of Excellence in Chemical Methodologies and Library Development [P50 GM069663]
- Scientific and Technological Research Council of Turkey (TUBITAK)
- OYP-Yuzuncu Yil University
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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.
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