Gold-Catalyzed [4 + 1] Heterocyclization of Hydroxamic Acid and Nonactivated Alkyne: A Protocol to Construct 5-Methyl-1,4,2-dioxazole
Xiao-Lin He, Xin-Ran Ma, Nan Yan* and Xiao-Wei Zhang*
*National Engineering Research Center for Carbohydrate Synthesis, Jiangxi Normal University, 99 Ziyang Road, Nanchang 330022, China,
Email: yannan104
163.com, xwzhangjxnu.edu.cn
X.-L. He, X.-R. Ma, N. Yan, X.-W. Zhang, J. Org. Chem., 2023, 88, 433-441.
DOI: 10.1021/acs.joc.2c02427
Abstract
A gold-catalyzed [4 + 1] heterocyclization of nonactivated alkyne and hydroxamic acids provides 5-methyl-1,4,2-dioxazoles. This method offers high efficiency, simple operation, mild reaction conditions, and good functional group compatibility. Moreover, gram-scale synthesis and synthetic application toward bioactive molecular skeletons have been realized.
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proposed mechanism
Key Words
N-heterocycles, O-heterocycles
ID: J42-Y2023
