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Synthesis 2022; 54(05): 1309-1320
DOI: 10.1055/s-0040-1720890
paper

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 AffiliationsWe 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.
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Abstract

An environmentally benign cascade redox process was developed for the efficient construction of the pharmaceutically significant spirocyclic tetrahydroquinolines via sequential SNAr/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

Accepted after revision: 30 August 2021

Article published online:
25 October 2021

© 2021. Thieme. All rights reserved

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