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

共 50 条

[1] Synthesis of Fluorenes via the Palladium-Catalyzed 5-exo-dig Annulation of o-Alkynylbiaryls
Chernyak, Natalia
Gevorgyan, Vladimir
ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (7-8) : 1101 - 1114
[2] Synthesis of Tribenzo[b,d,f]azepines via Palladium-Catalyzed Annulation Reaction of 2-Iodobiphenyls with 2-Halogenoanilines
Fang, Mao-Ying
Chen, Li-Ping
Huang, Lin
Fang, Dong-Mei
Chen, Xiao-Zhen
Wang, Bi-Qin
Feng, Chun
Xiang, Shi-Kai
JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (13) : 9096 - 9106
[3] The synthesis of quinolines via denitrogenative palladium-catalyzed cascade reaction of o-aminocinnamonitriles with arylhydrazines
Xie, Jing
Huang, Hang
Xu, Tong
Li, Renhao
Chen, Jiuxi
Ye, Xueting
RSC ADVANCES, 2020, 10 (15) : 8586 - 8593
[4] Cascade Reaction for the Synthesis of Carbolines from O-Methylketoximes and Styrenes via Palladium-Catalyzed C-H Activation and Sequential Annulation
Fu, Xiao-Pan
Tang, Shi-Biao
Yang, Jin-Yue
Zhang, Li-Li
Xia, Cheng-Cai
Ji, Ya-Fei
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (34) : 5974 - 5977
[5] Synthesis of aromatic ring fused pyrrole derivatives by palladium-catalyzed annulation of o-iodoarylamines with allyl acetate
Hong, CS
Seo, JY
Yum, EK
Sung, ND
HETEROCYCLES, 2004, 63 (03) : 631 - 639
[6] Palladium-catalyzed [4+3] annulation of 2-bromobiphenyls and epoxides for the assembly of dihydrodibenzo[b,d]oxepines
Shen, Zipei
Zhou, Lan
Wu, Chenggui
Zhou, Qianghui
Cheng, Hong-Gang
ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (45) : 8869 - 8872
[7] Convenient Access to C10-and C11-(di)arylated dibenzo[b,f]azepines via Palladium-catalyzed C-H Bonds Cleavages
Li, Haoran
Roisnel, Thierry
Soule, Jean-Francois
Doucet, Henri
ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (04) : 791 - 802
[8] Diastereoselective Synthesis of Dibenzo[b,d]azepines by Pd(II)-Catalyzed [5+2] Annulation of o-Arylanilines with Dienes
Bai, Lu
Wang, Yan
Ge, Yicong
Liu, Jingjing
Luan, Xinjun
ORGANIC LETTERS, 2017, 19 (07) : 1734 - 1737
[9] Highly Stereoselective Synthesis of Imine-Containing Dibenzo[b,d]azepines by a Palladium(II)-Catalyzed [5+2] Oxidative Annulation of o-Arylanilines with Alkynes
Zuo, Zhijun
Liu, Jingjing
Nan, Jiang
Fan, Liangxin
Sun, Wei
Wang, Yaoyu
Luan, Xinjun
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (51) : 15385 - 15389
[10] Synthesis of Dihydrobenzofurans via Palladium-Catalyzed Annulation of 1,3-Dienes by o-Iodoaryl Acetates
Rozhkov, Roman V.
Larock, Richard C.
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (12) : 4131 - 4134

← 1 2 3 4 5 →