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Quinazoline Synthesis via Rh(III)-Catalyzed Intermolecular C-H Functionalization of Benzimidates with Dioxazolones

Jie Wang, Shanke Zha, Kehao Chen, Feifei Zhang, Chao Song and Jin Zhu*

*School of Chemistry and Chemical Engineering, State Key Laboratory of Coordination Chemistry, Nanjing University, Nanjing 210093, China, Email: jinznju.edu.cn

J. Wang, S. Zha, K. Chen, F. Zhang, C. Song, J. Zhu, Org. Lett., 2016, 18, 2062-2065.

DOI: 10.1021/acs.orglett.6b00691 (free Supporting Information)


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Abstract

In an efficient redox-neutral [Cp*RhCl2]2/AgBF4 catalyzed double C-N bond formation sequence to prepare highly substituted quinazolines from benzimidates and dioxolanes as coupling partners, dioxazolones work as an internal oxidant to maintain the catalytic cycle. N-Unsubstituted imine not only acts as a directing group but also functions as a nucleophile in the postcoupling cyclization.

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proposed reaction pathway



Key Words

quinazolines


ID: J54-Y2016