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Highly Selective Synthesis of Dihydrobenzo[d]isoxazoles and Dihydrobenzo[d]oxazoles from Oximes and Arynes via in Situ Generation of Nitrones

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journal contribution
posted on 31.05.2017, 20:04 authored by Tuanli Yao, Beige Ren, Bo Wang, Yanna Zhao
An efficient method for the synthesis of dihydrobenzo­[d]­isoxazoles and dihydrobenzo­[d]­oxazoles bearing a quaternary carbon center has been developed. The reaction involves generation of a ketonitrone intermediate in situ from a ketoxime and an aryne. A novel thermal rearrangement of the dihydrobenzo­[d]­isoxazole products to the corresponding dihydrobenzo­[d]­oxazoles has been observed. These transformations tolerate a variety of functional groups and offer a rapid and efficient way to diverse dihydrobenzo­[d]­isoxazoles and dihydrobenzo­[d]­oxazoles under mild transition-metal-free conditions.