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Double‐Oxidative Dehydrogenative (DOD) Cyclization of Glycine Derivatives with Dioxane under Metal‐Free Aerobic Conditions
Author(s) -
Huo Congde,
Xie Haisheng,
Chen Fengjuan,
Tang Jing,
Wang Yajun
Publication year - 2016
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201500893
Subject(s) - chemistry , aromatization , glycine , quinoline , yield (engineering) , oxidative phosphorylation , combinatorial chemistry , quinoxaline , molecular oxygen , green chemistry , tandem , radical , oxygen , organic chemistry , reaction mechanism , catalysis , amino acid , biochemistry , materials science , metallurgy , composite material
The first carbon tetrabromide‐promoted novel double‐oxidative dehydrogenative cyclization/acidic ring opening/aromatization tandem reaction of glycine derivatives with dioxane for the synthesis of complex quinoline motifs has been developed (up to 71% yield). The use of very inexpensive substrates (glycine derivatives and dioxane) and an extremely simple metal‐free promoter (carbon tetrabromide) with green molecular oxygen (air) as an oxidant make this protocol very attractive for potential synthetic applications. A plausible mechanism involving a radical process is proposed.