Synthesis 2022; 54(05): 1309-1320
Facile Synthesis of Spirocyclic Tetrahydroquinolines via C(sp3 )–H Functionalization in a Cascade Redox Process
Liping Yu
a
College of Chemical Engineering, Qingdao University of Science and Technology, Qingdao 266042, P. R. of China
c
College of Landscape and Forestry, Qingdao Agricultural University, Qingdao 266109, P. R. of China
,
Bin Qiu
b
College of Chemistry and Pharmaceutical Sciences, Qingdao Agricultural University, Qingdao 266109, P. R. of China
,
Peizhen Dong
b
College of Chemistry and Pharmaceutical Sciences, Qingdao Agricultural University, Qingdao 266109, P. R. of China
,
Jian Xiao∗
b
College of Chemistry and Pharmaceutical Sciences, Qingdao Agricultural University, Qingdao 266109, P. R. of China
,
Shitao Yu∗
a
College of Chemical Engineering, Qingdao University of Science and Technology, Qingdao 266042, P. R. of China
› Author Affiliations We are grateful to the Taishan Scholar Project of Shandong Province (tsqn201909131, ts201511033), NSFC (21878167), and The Key Research Foundation of Science of Shandong Province (ZR2020KB007). Project support by the Natural Science Foundation of Shandong Province (ZR2020QB047) and the Key Research and Development Program of Qingdao Technical College (2020ZDYF06) are also gratefully acknowledged.
Abstract
An environmentally benign cascade redox process was developed for the efficient construction of the pharmaceutically significant spirocyclic tetrahydroquinolines via sequential SN Ar/Knoevenagel condensation/[1,5]-hydride transfer/cyclization. This green transformation has the features of being catalyst-free, additive-free, operationally simple, and has high step- and atom-economy.
Key words
tetrahydroquinoline -
C–H functionalization -
cascade reaction -
hydride transfer
Supporting Information
Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1720890.
Supporting Information
Publication History
Received: 28 July 2021
© 2021. Thieme. All rights reserved
Georg Thieme Verlag KG
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