Synthesis of Dibenzo[b,f]azepines via Palladium-Catalyzed Cascade [4+3] Annulation of o-Alkenyl Bromoarenes and o-Bromoaniline Derivatives

被引：2
|
作者：
Zhan, Xin-Chen [1 ]
Lin, Guo-Qiang [1 ,2 ]
Fu, Jian-Guo [1 ]
Ji, Xiao-Ming [1 ]
Zhang, Shu-Sheng [1 ]
Feng, Chen-Guo [1 ,2 ]
机构：
[1] Shanghai Univ Tradit Chinese Med, Innovat Res Inst Tradit Chinese Med, Res Ctr Chiral Drugs, Shanghai Frontiers Sci Ctr TCM Chem Biol, Shanghai 201203, Peoples R China
[2] Univ Chinese Acad Sci, Shanghai Inst Organ Chem, Ctr Excellence Mol Synth, Key Lab Synthet Chem Nat Subst, Shanghai 200032, Peoples R China
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2023年 / 365卷 / 23期
基金：
中国国家自然科学基金;
关键词：
annulation; dibenzo[b; f]azepines; palladacycle; cascade reaction; palladium; C-H activation; REMOTE METALATION; OXCARBAZEPINE; HETEROCYCLES; ARYL; ARYLATION; BOND;
D O I：
10.1002/adsc.202300336
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
A cascade [4+3] annulation of o-alkenyl bromoarenes and o-bromoaniline derivatives was described. Various dibenzo[b,f]azepines with substitutions on the 10/11 position were obtained in 14-97% yields. The synthetic versatility of this protocol is highlighted by the preparation of a precursor of the drug molecule oxcarbazepine, a gram-scale synthesis, and two product transformations. Unlike previous amination/Heck sequence, this cascade process is supposed to undergo a C(vinyl), C(aryl)-palladacycle involved pathway.
引用
收藏
页码：4127 / 4131
页数：5
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