通过芳炔与恶唑啉的 [3 + 2] 环加成反应合成二氢苯并异恶唑。
Synthesis of dihydrobenzisoxazoles by the [3 + 2] cycloaddition of arynes and oxaziridines.
机构信息
Department of Chemistry, Iowa State University, Ames, Iowa 50011, United States.
出版信息
J Org Chem. 2010 Nov 5;75(21):7381-7. doi: 10.1021/jo101656c.
Abstract
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.
摘要
二氢苯并恶唑可通过氮丙啶和芳炔的[3+2]环加成反应以较好的收率轻易制备。该反应涉及氮丙啶的 C-O 键的不寻常断裂，并且对氮丙啶和邻-(三甲基甲硅烷基)芳基三氟甲磺酸酯上的各种取代基具有耐受性，以形成芳基、杂芳基、烷基和萘基取代的二氢苯并恶唑。所得卤代二氢苯并恶唑可通过钯催化交叉偶联过程轻易地进行进一步的复杂产物的合成。
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