Rhodium(III)-catalyzed oxidative annulation of N-arylbenzamidines with maleimides via dual C-H activation

被引:7
作者
Sankaram, G. Siva [1 ,3 ]
Sahoo, Tanmoy [1 ,3 ]
Sridhar, B. [2 ]
Reddy, B. V. Subba [1 ]
机构
[1] CSIR Indian Inst Chem Technol, Fluoroagrochem, Hyderabad, India
[2] CSIR Indian Inst Chem Technol, Lab X ray Crystallog, Hyderabad, India
[3] Acad Sci & Innovat Res AcSIR, Ghaziabad, UP, India
关键词
FUNCTIONALIZATION; AMIDINES; HETEROCYCLES; IMIDAZOLES; IMIDAMIDES;
D O I
10.1039/d2ob01972h
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An oxidative annulation of N-arylbenzimidamides with maleimides has been developed for the first time using a catalytic amount of the [Cp*RhCl2](2) complex for the synthesis of a diverse range of 1H-benzo[4,5]imidazo[2,1-a]pyrrolo[3,4-c]isoquinoline-1,3(2H)-dione derivatives. This method is versatile and atom-economical for producing polycyclic benzo[4,5]imidazo[2,1-a]pyrrolo[3,4-c] isoquinoline-1,3(2H)-dione scaffolds in a single step.
引用
收藏
页码:1719 / 1724
页数:6
相关论文
共 39 条
  • [11] Recent Methodologies That Exploit C-C Single-Bond Cleavage of Strained Ring Systems by Transition Metal Complexes
    Fumagalli, Gabriele
    Stanton, Steven
    Bower, John F.
    [J]. CHEMICAL REVIEWS, 2017, 117 (13) : 9404 - 9432
  • [12] Synthesis of aminoisoquinolines via Rh-catalyzed [4+2] annulation of benzamidamides with vinylene carbonate
    Huang, Xin
    Xu, Yingying
    Li, Jianglian
    Lai, Ruizhi
    Luo, Yi
    Wang, Qiantao
    Yang, Zhongzhen
    Wu, Yong
    [J]. CHINESE CHEMICAL LETTERS, 2021, 32 (11) : 3518 - 3521
  • [13] Transition-Metal-Catalyzed C-H Bond Addition to Carbonyls, Imines, and Related Polarized π Bonds
    Hummel, Joshua R.
    Boerth, Jeffrey A.
    Ellman, Jonathan A.
    [J]. CHEMICAL REVIEWS, 2017, 117 (13) : 9163 - 9227
  • [14] IKEDA Y, 1979, ARZNEIMITTEL-FORSCH, V29-1, P511
  • [15] Chemistry and Properties of Indolocarbazoles
    Janosik, Tomasz
    Rannug, Agneta
    Rannug, Ulf
    Wahlstrom, Niklas
    Slatt, Johnny
    Bergman, Jan
    [J]. CHEMICAL REVIEWS, 2018, 118 (18) : 9058 - 9128
  • [16] Minor structural modifications to Pracinostat produce big changes in its biological responses
    Jia, Rong
    Sun, Pengju
    Zhang, Yan
    Ge, Youjin
    Yu, Niefang
    [J]. CHEMICAL BIOLOGY & DRUG DESIGN, 2019, 94 (02) : 1488 - 1493
  • [17] Synthesis of Quinazolin-4(3H)-ones via Amidine N-Arylation
    Li, Bryan
    Samp, Lacey
    Sagal, John
    Hayward, Cheryl M.
    Yang, Christine
    Zhang, Zhijun
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (03) : 1273 - 1277
  • [18] Amidines for Versatile Cobalt(III)-Catalyzed Synthesis of Isoquinolines through C-H Functionalization with Diazo Compounds
    Li, Jie
    Tang, Mengyao
    Zang, Lei
    Zhang, Xiaolei
    Zhang, Zhao
    Ackermann, Lutz
    [J]. ORGANIC LETTERS, 2016, 18 (11) : 2742 - 2745
  • [19] Ruthenium(II)-Catalyzed C-H Activation of Imidamides and Divergent Couplings with Diazo Compounds: Substrate-Controlled Synthesis of Indoles and 3H-Indoles
    Li, Yunyun
    Qi, Zisong
    Wang, He
    Yang, Xifa
    Li, Xingwei
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (39) : 11877 - 11881
  • [20] Rhodium(III)-Catalyzed Oxidative Annulation of Amidines with Alkynes via Sequential C-H Bond Activation
    Meng, Yan-Yu
    Zhu, Wen-Jing
    Song, Yuan-Yuan
    Bu, Gang-Gang
    Zhang, Li-Juan
    Xu, Fen
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (08) : 1290 - 1294