PIFA介导的α-酰基-β-氨基丙烯酰胺的串联霍夫曼型重排和环化反应：通向多取代恶唑-2(3)-酮的方法
PIFA-Mediated Tandem Hofmann-Type Rearrangement and Cyclization Reaction of α-Acyl-β-aminoacrylamides: Access to Polysubstituted Oxazol-2(3)-ones.
作者信息
Li Baibin, Yuan Jingwen, Ye Xuebei, Zhang Rui, Li Jiacheng, Wang Yu, Hu Jiana, Dong Dewen
机构信息
CAS Key Laboratory of High-Performance Synthetic Rubber and Its Composite Materials, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, P. R. China.
University of Science and Technology of China, Hefei 230026, P. R. China.
出版信息
J Org Chem. 2021 Dec 17;86(24):17944-17954. doi: 10.1021/acs.joc.1c02276. Epub 2021 Dec 6.
An efficient and straightforward synthesis of polysubstituted oxazol-2(3)-ones has been developed via a tandem Hofmann-type rearrangement and cyclization reaction of various α-acyl-β-aminoacrylamides mediated by phenyl iodine(III) bis(trifluoroacetate) (PIFA) in the presence of trifloroacetic acid (TFA). This novel protocol features readily available starting materials, mild reaction conditions, simple execution, high chemoselectivity, good functional group tolerance, and a metal-free oxidation process.
通过在三氟乙酸（TFA）存在下，由双（三氟乙酸）苯基碘（III）（PIFA）介导的各种α-酰基-β-氨基丙烯酰胺的串联霍夫曼型重排和环化反应，开发了一种高效且直接的多取代恶唑-2（3）-酮的合成方法。该新颖的方法具有起始原料易于获得、反应条件温和、操作简单、化学选择性高、官能团耐受性好以及无金属氧化过程等特点。
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