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

页码：4127 / 4131

页数：5

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