A Nickel(II) Chloride and Tetrahydroxydiboron Cocatalyzed Facile Synthesis of Benzo[b]azepines with an Appended Fluorinated Side Chain

被引:0
|
作者
Lei, Wenqing [1 ]
Yang, Yingfan [1 ]
Guo, Minjie [2 ]
Zhao, Wentao [1 ]
Wang, Guangwei [1 ]
机构
[1] Tianjin Univ, Tianjin Key Lab Mol Optoelect Sci, Dept Chem, Sch Sci, Tianjin 300072, Peoples R China
[2] Tianjin Univ, Inst Mol Design & Synth, Sch Pharmaceut Sci & Technol, Tianjin 300072, Peoples R China
来源
SYNTHESIS-STUTTGART | 2023年 / 55卷 / 17期
基金
中国国家自然科学基金;
关键词
tetrahydroxydiboron; ethyl bromodifluoroacetate; nickel catalyst; radical cascade; benzo[b]azepines; RADICAL CYCLIZATION; DIFLUOROALKYLATION; PHARMACEUTICALS; 1-BENZAZEPINES; IMIPRAMINE; SCAFFOLDS;
D O I
10.1055/a-2096-7045
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel nickel-catalyzed chemoselective cascade reaction strategy towards the synthesis of benzo[b]azepines was developed. The method is characterized by simple and mild conditions, low cost, and a wide range of substrates. This method enabled the facile and efficient synthesis of a series of 2,3,4,5-tetrahydro-1H-benzo[b]azepine analogues with an appended fluorinated side chain.
引用
收藏
页码:2702 / 2712
页数:11
相关论文
共 14 条
  • [1] Palladium(II)/Lewis Acid Cocatalyzed Oxidative Annulation of 2-Alkenylanilines and Propargylic Esters: An Access to Benzo[b]azepines
    Qiao, Hong
    Zhang, Shengjun
    Li, Kangkang
    Cao, Zhengqiang
    Zeng, Fanlong
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (17): : 10843 - 10851
  • [2] Facile Synthesis of 1-Methyl-1H-benzo[b]azepines from 1-Methylquinolinium Iodides and Diazo(trimethylsilyl)methylmagnesium Bromide
    Morita, Mikio
    Hari, Yoshiyuki
    Aoyama, Toyohiko
    SYNTHESIS-STUTTGART, 2010, (24): : 4221 - 4227
  • [3] CARB 104-Toward the synthesis of side chain B of rhamnogalacturonan II
    Nepogodiev, Sergey
    De Oliveira, Marcelo T.
    Field, Rob
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 233 : 550 - 550
  • [4] Synthesis and immunological properties of a tetrasaccharide portion of the B side chain of rhamnogalacturonan II (RG-II)
    Rao, Yu
    Buskas, Therese
    Albert, Anathea
    O'Neill, Malcolm A.
    Hahn, Michael G.
    Boons, Geert-Jan
    CHEMBIOCHEM, 2008, 9 (03) : 381 - 388
  • [5] Synthesis and Characterization of Nickel(II) Salphen Complex with Piperidine Side Chain and Interaction Study with Dengue DNA
    Ariffin, Eda Yuhana
    Heng, Lee Yook
    Ling, Tan Ling
    Abd Karim, Nurulhuda
    SAINS MALAYSIANA, 2018, 47 (06): : 1139 - 1146
  • [6] Efficient polymer solar cells based on a new benzo[1,2-b:4,5-b′]dithiophene derivative with fluorinated alkoxyphenyl side chain
    Chen, Weichao
    Du, Zhengkun
    Han, Liangliang
    Xiao, Manjun
    Shen, Wenfei
    Wang, Ting
    Zhou, Yuanhang
    Yang, Renqiang
    JOURNAL OF MATERIALS CHEMISTRY A, 2015, 3 (06) : 3130 - 3135
  • [7] Palladium/Nickel-Cocatalyzed Cycloaddition of 1,3-Dehydro-o-Carborane with Alkynes. Facile Synthesis of C,B-Substituted Carboranes
    Qiu, Zaozao
    Xie, Zuowei
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (45) : 16085 - 16093
  • [8] A Facile Synthesis and Crystallographic Analysis of Seven Trityl Phosphorus Compounds and Two Nickel(II) Phosphine Side-Products
    Gushwa, Audra F.
    Belabassi, Yamina
    Montchamp, Jean-Luc
    Richards, Anne F.
    JOURNAL OF CHEMICAL CRYSTALLOGRAPHY, 2009, 39 (05) : 337 - 347
  • [9] A Facile Synthesis and Crystallographic Analysis of Seven Trityl Phosphorus Compounds and Two Nickel(II) Phosphine Side-Products
    Audra F. Gushwa
    Yamina Belabassi
    Jean-Luc Montchamp
    Anne F. Richards
    Journal of Chemical Crystallography, 2009, 39 : 337 - 347
  • [10] Facile method for the hydrolysis of a nickel Schiff base complex useful for synthesis of side-chain protected unnatural amino acids
    Bontrager, Cory
    Geibel, Tanner
    Lengyel, George
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 252