Facile Synthesis of Spirocyclic Tetrahydroquinolines via C(sp3)–H Functionalization in a Cascade Redox Process

Liping Yu; Bin Qiu; Peizhen Dong; Jian Xiao; Shitao Yu

doi:10.1055/s-0040-1720890

Synthesis, Table of Contents

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

^aCollege of Chemical Engineering, Qingdao University of Science and Technology, Qingdao 266042, P. R. of China

^cCollege of Landscape and Forestry, Qingdao Agricultural University, Qingdao 266109, P. R. of China

,

Bin Qiu

^bCollege of Chemistry and Pharmaceutical Sciences, Qingdao Agricultural University, Qingdao 266109, P. R. of China

,

Peizhen Dong

^bCollege of Chemistry and Pharmaceutical Sciences, Qingdao Agricultural University, Qingdao 266109, P. R. of China

,

Jian Xiao∗

^bCollege of Chemistry and Pharmaceutical Sciences, Qingdao Agricultural University, Qingdao 266109, P. R. of China

,

Shitao Yu∗

^aCollege of Chemical Engineering, Qingdao University of Science and Technology, Qingdao 266042, P. R. of China

› Author Affiliations

Abstract

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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 S_NAr/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

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References

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