Catalyst-Free α-Alkylation-α-Hydroxylation of Oxindole with Alcohols

Siwei Wu, Wei Song, Runyu Zhu, Jingwen Hu, Lin Zhao, Zheyao Li, Xinhong Yu*, Chengcai Xia* and Jianhong Zhao*

*East China University of Science & Technology, Shanghai 200237; Taishan Medical University, Taian, Shandong 271016, China, Email: xhyuecust.edu.cn, xiachc163.com, zjhpharm163.com

S. Wu. W. Song, R. Zhu, J. Hu, L. Zhao, Z. Li, X. Yu, C. Xia, J. Zhao, J. Org. Chem., 2022, 87, 5464-5471.

DOI: 10.1021/acs.joc.1c02185

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Abstract

3-Alkyl-3-hydroxyoxindoles have antioxidant, neuroprotective, anticancer, and anti-HIV activities. α-Alkylation-α-hydroxylation of oxindoles with benzyl alcohols enables an economical synthesis without using any transition-metal catalysts in very good yields.

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proposed mechanism

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Key Words

Oxindoles, Oxygen

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ID: J42-Y2022