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

Autor: Duan P; Key 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., Sun J; Key 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., Zhu Z; Clinical Research Center, Integrated Hospital of Traditional Chinese Medicine, Southern Medical University, Guangzhou, 510315, P. R. China., Zhang M; Key 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.
Jazyk: angličtina
Zdroj: Organic & biomolecular chemistry [Org Biomol Chem] 2023 Jan 04; Vol. 21 (2), pp. 397-401. Date of Electronic Publication: 2023 Jan 04.
DOI: 10.1039/d2ob02066a
Abstrakt: 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.
Databáze: MEDLINE