General Synthesis of Fully Substituted 4-Aminooxazoles from Amides and 1,4,2-Dioxazol-5-ones Based on Amide Activation and Umpolung Process
Yunxiang Weng, Lin Min, Lidong Shan, Hongchen Li, Xinyan Wang* and Yuefei Hu*
*Department of Chemistry, Tsinghua University, Beijing 100084, P. R. China,
Email: wangxinyan
mail.tsinghua.edu.cn, yfhmail.tsinghua.edu.cn
Y. Weng, L. Min, L. Shan, H. Li, X. Wang, Y. Hu, J. Org. Chem., 2021, 86, 199-206.
DOI: 10.1021/acs.joc.0c02015
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Abstract
The combination of amide activation and an umpolung reaction enables a general and efficient synthesis of fully substituted 4-aminooxazoles under mild conditions from amides and 1,4,2-dioxazol-5-ones as a rare type of umpolung reagent bearing a nucleophilic N-atom. The 1,4,2-dioxazol-5-one acts as an umpolung reagent, a substrate, and a weak base.
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proposed mechanism
Key Words
ID: J42-Y2021
