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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
Organic Letters ( IF 4.9 ) Pub Date : 2017-05-31 00:00:00 , DOI: 10.1021/acs.orglett.7b01260 Tuanli Yao 1 , Beige Ren 1 , Bo Wang 1 , Yanna Zhao 1
Organic Letters ( IF 4.9 ) Pub Date : 2017-05-31 00:00:00 , DOI: 10.1021/acs.orglett.7b01260 Tuanli Yao 1 , Beige Ren 1 , Bo Wang 1 , Yanna Zhao 1
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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.
中文翻译：
通过肟生成的硝基化合物选择性合成肟和芳烃二氢苯并[ d ]异恶唑和二氢苯并[ d ]恶唑。
开发了一种有效的合成带有季碳中心的二氢苯并[ d ]异恶唑和二氢苯并[ d ]恶唑的方法。该反应涉及由酮肟和芳烃原位产生酮硝基中间体。已经观察到二氢苯并[ d ]异恶唑产物向相应的二氢苯并[ d ]恶唑的新颖的热重排。这些转变可耐受多种官能团，并在无过渡金属的条件下为各种二氢苯并[ d ]异恶唑和二氢苯并[ d ]恶唑提供了快速有效的方法。
更新日期：2017-05-31
中文翻译：
通过肟生成的硝基化合物选择性合成肟和芳烃二氢苯并[ d ]异恶唑和二氢苯并[ d ]恶唑。
开发了一种有效的合成带有季碳中心的二氢苯并[ d ]异恶唑和二氢苯并[ d ]恶唑的方法。该反应涉及由酮肟和芳烃原位产生酮硝基中间体。已经观察到二氢苯并[ d ]异恶唑产物向相应的二氢苯并[ d ]恶唑的新颖的热重排。这些转变可耐受多种官能团，并在无过渡金属的条件下为各种二氢苯并[ d ]异恶唑和二氢苯并[ d ]恶唑提供了快速有效的方法。
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