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Silver-Mediated Cyanomethylation of Cinnamamides by Direct C(sp3)–H Functionalization of Acetonitrile

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Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, China
School of Pharmacy, Hubei University of Chinese Medicine, Wuhan 430065, China
Cite this: J. Org. Chem. 2018, 83, 3, 1525–1531
Publication Date (Web):January 9, 2018
https://doi.org/10.1021/acs.joc.7b02585
Copyright © 2018 American Chemical Society

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    Abstract

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    An efficient, silver-induced tandem radical addition/cyclization for the synthesis of 3,4-dihydroquinolinones is presented, which exhibits a good functional group tolerance. The reaction is easy to operate and amenable to a multigram-scale synthesis. Additionally, this work illustrates the formation of a key skeleton for the synthesis of biologically interesting 3,4-dihydroquinolinone alkaloids.

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    This article is cited by 24 publications.

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    3. Mengyang Shen, Jie Zhao, Yuanshuang Xu, Xinying Zhang, Xuesen Fan. Synthesis of Dihydroquinolinone Derivatives via the Cascade Reaction of o-Silylaryl Triflates with Pyrazolidinones. The Journal of Organic Chemistry 2021, 86 (21) , 15203-15216. https://doi.org/10.1021/acs.joc.1c01814
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