Issue 2, 2023

Selective access to fused tetrahydroquinolines via a copper-catalysed oxidative three-component annulation reaction

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.

Graphical abstract: Selective access to fused tetrahydroquinolines via a copper-catalysed oxidative three-component annulation reaction

Supplementary files

Article information

Article type
Paper
Submitted
11 Nov 2022
Accepted
06 Dec 2022
First published
07 Dec 2022

Org. Biomol. Chem., 2023,21, 397-401

Selective access to fused tetrahydroquinolines via a copper-catalysed oxidative three-component annulation reaction

P. Duan, J. Sun, Z. Zhu and M. Zhang, Org. Biomol. Chem., 2023, 21, 397 DOI: 10.1039/D2OB02066A

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