tert-Butyl Hydroperoxide Promoted the Reaction of Quinazoline-3-oxides with Primary Amines Affording Quinazolin-4(3H)-ones

Jin Luo*, Juelin Wan, Lianlian Wu, Lingyun Yang and Tao Wang*

*Jiangxi Province Key Laboratory of Chemical Biology, College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang, Jiangxi 330022, P. R. China, Email: wangtaojxnu.edu.cn

J. Luo, J. Wan, L. Wu, L. Yang, T. Wang, J. Org. Chem., 2022, 87, 9864-9874.

DOI: 10.1021/acs.joc.2c00898

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Abstract

An efficient and facile reaction of quinazoline-3-oxides with primary amines provides a broad range of quinazolin-4(3H)-ones under metal-free and mild reaction conditions employing tert-butyl hydroperoxide as the oxidant. Remarkably, a precursor for the synthesis of bioactive evodiamine and rutaempine was conveniently obtained in good yield.

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proposed mechanism

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Key Words

quinazolin-4(3H)-ones, tert-butyl hydroperoxide

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ID: J42-Y2022