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Updated: Aug 17, 2025

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Selective access to fused tetrahydroquinolines via a copper-catalysed oxidative three-component annulation reaction
Peng Duan1, Jialu Sun1, Zhibo Zhu2
1Key Lab of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology, Wushan Rd-381, Guangzhou 510641, People's Republic of China. minzhang@scut.edu.cn.
Abstract:
Via a copper-catalyzed three-component annulation reaction, we herein report a new method for the direct and syn-selective construction of cyclic ether-fused tetrahydroquinolines from readily available secondary anilines, saturated five or six-membered cyclic ethers, and paraformaldehyde. The synthesis features operational simplicity, excellent step and atom efficiency, good functionality and substrate compatibility. In comparison with the reported synthetic protocols capable of synthesizing N-alkyl fused tetrahydroquinolines, this newly developed chemistry allows access to both N-alkyl and N-aryl products. The current work complements the preparation of fused tetrahydroquinolines.
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