Transition-Metal-Free Approach to Acridone Derivatives by TBHP-Promoted Oxidative Annulation of Isatins with Arynes

Min Luo, Nana Dong, Mengyao Zhu, Yongfeng Wang, Cheng Xu* and Guodong Yin*

*College of Chemistry and Chemical Engineering, Hubei Normal University, Huangshi 435002, P. R. China, Email: chemxuchenghbnu.edu.cn, gdyinhbnu.edu.cn

M. Luo, N. Dong, M. Zhu, Y. Wang, C. Xu, G. Yin, J. Org. Chem., 2023, 88, 9419-9423.

DOI: 10.1021/acs.joc.3c00250

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Abstract

tert-Butyl hydroperoxide promotes an oxidative annulation reaction of isatins with 2-(trimethylsilyl)aryl triflates for the convenient synthesis of acridone derivatives. The reaction may proceed via consecutive Baeyer-Villiger-type rearrangement followed by an intermolecular cyclization. This convenient method offers broad substrate scope and good functional group tolerance.

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proposed mechanism

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Key Words

Acridones, TBHP, Baeyer-Villiger oxidation

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ID: J42-Y2023