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Gold-Catalyzed Radical-Involved Intramolecular Cyclization of Internal N-Propargylamides for the Construction of 5-Oxazole Ketones

Hejun An, Shaoyu Mai, Qingqing Xuan, Yao Zhou, Qiuling Song*

*College of Chemical Engineering, College of Material Sciences Engineering at Huaqiao University, 668 Jimei Boulevard, Xiamen, Fujian 361021, People’s Republic of China, Email: qsonghqu.edu.cn

H. An, S. Mai, Q. Xuan, Y. Zhou, Q. Song, J. Org. Chem., 2019, 84, 401-408.

DOI: 10.1021/acs.joc.8b02334 (free Supporting Information)



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Abstract

The combination of gold catalysis and radical chemistry enables the synthesis of 5-oxazole ketones from internal N-propargylamides in the presence of 4-MeO-TEMPO as an oxidant. The desired 5-oxazole ketones were provided in good yields with an excellent functional group compatibility under mild conditions.

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proposed mechanism



Key Words

Oxazoles, 4-MeO-TEMPO, tBuONO


ID: J42-Y2019