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

[41] Palladium-Catalyzed Regioselective Synthesis of 1-Benzoazepine Carbonitriles from o-Alkynylanilines via 7-endo-dig Annulation and Cyanation
Dhandabani, Ganesh Kumar
Mutra, Mohana Reddy
Wang, Jeh-Jeng
ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (24) : 4754 - 4763
[42] Copper-Catalyzed Cascade Synthesis of 2-Aryl-3-cyanobenzofuran and Dibenzo[b,f]oxepine-10-carbonitrile Derivatives
Villuri, Bharath Kumar
Ichake, Sachin S.
Reddy, Sabbasani Rajasekhara
Kavala, Veerababurao
Bandi, Vijayalakshmi
Kuo, Chun-Wei
Yao, Ching-Fa
JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (17): : 10241 - 10247
[43] Highly Regio-, Diastereo-, and Enantioselective Assembly of Azepino[2,3-b]indoles via Palladium-Catalyzed [4+3] Cycloaddition
Yang, Wu-Lin
Huang, Zesheng
Liu, Yang-Zi
Yu, Xingxin
Deng, Wei-Ping
CHINESE JOURNAL OF CHEMISTRY, 2020, 38 (12) : 1571 - 1574
[44] Synthesis of Benzotriazepine Derivatives via [4+3] Cycloaddition of Aza-o-quinone Methide Intermediates and Azomethine Imines
Zhi, Ying
Zhao, Kun
Shu, Tao
Enders, Dieter
SYNTHESIS-STUTTGART, 2016, 48 (02): : 238 - 244
[45] Palladium-Catalyzed Regioselective Synthesis of 1,2-Fused Indole-Diazepines via [5+2] Annulation of o-Indoloanilines with Alkynes
Thikekar, Tushar Ulhas
Sun, Chung-Ming
ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (19) : 3388 - 3396
[46] Synthesis of 2-Aminobenzoxazoles and 3-Aminobenzoxazines via Palladium-Catalyzed Aerobic Oxidation of o-Aminophenols with Isocyanides
Liu, Bifu
Yin, Meizhou
Gao, Hanling
Wu, Wanqing
Jiang, Huanfeng
JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (07): : 3009 - 3020
[47] N-Heterocyclic Carbene Catalyzed [4+3] Annulation of Enals and o-Quinone Methides: Highly Enantioselective Synthesis of Benzo-ε-Lactones
Lv, Hui
Jia, Wen-Qiang
Sun, Li-Hui
Ye, Song
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (33) : 8607 - 8610
[48] Palladium-catalyzed highly stereoselective synthesis of N-aryl-3-arylmethylisoxazolidines via tandem arylation of O-homoallylhydroxylamines
Peng, Jinsong
Lin, Wenqing
Yuan, Shixue
Chen, Yuanwei
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (08): : 3145 - 3148
[49] Efficient Synthesis of 5H-Cyclopenta[c]quinoline Derivatives via Palladium-Catalyzed Domino Reactions of o-Alkynylhalobenzene with Amine
Luo, Yong
Pan, Xiaolin
Wu, Jie
ORGANIC LETTERS, 2011, 13 (05) : 1150 - 1153
[50] SYNTHESIS OF ARYL-SUBSTITUTED 3-ALKENAMIDES VIA PALLADIUM-CATALYZED CROSS-COUPLING OF ARYL IODIDES AND 4-ALKENYL-2-AZETIDINONES
LAROCK, RC
DING, S
TETRAHEDRON LETTERS, 1993, 34 (06) : 979 - 982

← 1 2 3 4 5 →