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Radical C−H Bond Oxidation Initiated Intramolecular Cyclization of Glycine Esters: Construction of Dihydroquinoline Skeletons
Author(s) -
Chen Qian,
Zhang Shuwei,
Zhang Ting,
He Kaixuan,
Yuan Yu,
Jia Xiaodong
Publication year - 2019
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201800596
Subject(s) - chemistry , intramolecular force , glycine , salt (chemistry) , radical , radical cyclization , medicinal chemistry , nitrogen , stereochemistry , organic chemistry , polymer chemistry , amino acid , biochemistry
An efficient construction of dihydroquinoline derivatives was realized through radical cation salt‐initiated C−H bond oxidation of unsaturated glycine esters. In the presence of dioxygen, the sp 3 C−H bond adjacent to nitrogen was oxidized, followed by cascade cyclization, affording the desired dihydroquinoline products. The mechanistic investigation revealed that a radical intermediate was involved in this reaction.