Facile synthesis of annulated heterocyclic benzo[kl]acridine derivatives via one-pot N-H/C-H coupling

被引:8
|
作者
Zagranyarski, Yulian [1 ,2 ]
Skabeev, Artem [1 ]
Ma, Yingjie [1 ]
Muellen, Klaus [1 ,3 ]
Li, Chen [1 ]
机构
[1] Max Planck Inst Polymer Res, Ackermannweg 10, D-55128 Mainz, Germany
[2] Sofia Univ St Kliment Ohridski, Fac Chem & Pharm, 1 James Bourchier Ave, Sofia 1164, Bulgaria
[3] Johannes Gutenberg Univ Mainz, Inst Phys Chem, Duesbergweg 10-14, D-55128 Mainz, Germany
来源
ORGANIC CHEMISTRY FRONTIERS | 2016年 / 3卷 / 11期
关键词
CARBAZOLES; ACTIVATION; INDOLES; NITRO; REDUCTION; KETONES;
D O I
10.1039/c6qo00371k
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient N-H/C-H one-pot coupling method for the preparation of benzo[kl]acridines has been developed based on palladium-catalyzed domino synthesis. Using commercially available starting materials such as dihalonaphthalenes and diphenylamines, and combining amination with catalysts for C-H activation, up to 95% overall yield can be achieved.
引用
收藏
页码:1520 / 1523
页数:4
相关论文
共 50 条
  • [1] Heterocycle Synthesis via Direct C-H/N-H Coupling
    Nadres, Enrico T.
    Daugulis, Olafs
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (01) : 7 - 10
  • [2] Copper-catalyzed N-arylation and aerobic oxidative C-H/C-H coupling: one-pot synthesis of indoloimidazoquinoline derivatives
    Wang, Meng
    Jin, Yunhe
    Yang, Haijun
    Fu, Hua
    Hu, Liming
    [J]. RSC ADVANCES, 2013, 3 (22) : 8211 - 8214
  • [3] A practical one-pot procedure for the synthesis of N-H isoquinolones
    Lu, Shaonan
    Lin, Yingfu
    Zhong, Hongban
    Zhao, Kang
    Huang, Jianhui
    [J]. TETRAHEDRON LETTERS, 2013, 54 (15) : 2001 - 2005
  • [4] One-pot Synthesis of Benzo[c]acridine Derivatives Using SBA-Pr-SO3H as Nano Catalyst
    Ziarani, Ghodsi Mohammadi
    Mousavi, Somayeh
    Rahimifard, Mahshid
    Badiei, Alireza
    [J]. JOURNAL OF THE MEXICAN CHEMICAL SOCIETY, 2014, 58 (02) : 168 - 172
  • [5] One-pot Cascade Reaction for the Synthesis of Phenanthridines via Suzuki Coupling/C-H Oxidation/Aromatization
    Zhang, Yi
    Ding, Yuxin
    Chen, Rener
    Ma, Yongmin
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (24) : 5697 - 5707
  • [6] Pd-Catalyzed C-H/N-H Arylation: One-Pot Synthesis of Indolo[1,2-f]phenanthridines
    Kong, Lingkai
    Yao, Qiyi
    Wang, Mengdan
    Sun, Ruizhuo
    Li, Yanzhong
    [J]. CHEMISTRYSELECT, 2018, 3 (02): : 456 - 460
  • [7] Direct Amination of Azoles via Catalytic C-H, N-H Coupling
    Monguchi, Daiki
    Fujiwara, Taiki
    Furukawa, Hirotoshi
    Mori, Atsunori
    [J]. ORGANIC LETTERS, 2009, 11 (07) : 1607 - 1610
  • [8] Chemoselective one-pot synthesis of terphenyl derivatives by sequential directed C-H functionalization-Suzuki coupling
    Ren, Limin
    Chu, Wenyi
    Guan, Dinghui
    Hou, Yanjun
    Wang, Man
    Yuan, Xiaobin
    Sun, Zhizhong
    [J]. APPLIED ORGANOMETALLIC CHEMISTRY, 2014, 28 (09) : 673 - 677
  • [9] Electrocatalytic C-H/N-H Coupling of 2′-Aminoacetophenones for the Synthesis of Isatins
    Qian, Peng
    Su, Ji-Hu
    Wang, Yukang
    Bi, Meixiang
    Zha, Zhenggen
    Wang, Zhiyong
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (12): : 6434 - 6440
  • [10] ISOINDOLONE SYNTHESIS VIA INTRAMOLECULAR COUPLING OF BENZYLIC C-H BONDS WITH AMIDE N-H BONDS
    Zhang, Ming
    Chen, Tianbao
    Liu, Qinhua
    [J]. HETEROCYCLES, 2014, 89 (05) : 1255 - 1259