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
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2023年 / 21卷 / 08期
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
  • [1] Carboxylate-Assisted Ruthenium-Catalyzed Alkyne Annulations by C-H/Het-H Bond Functionalizations
    Ackermann, Lutz
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (02) : 281 - 295
  • [2] Proton-conducting membranes based on benzimidazole polymers for high-temperature PEM fuel cells. A chemical quest
    Antonio Asensio, Juan
    Sanchez, Eduardo M.
    Gomez-Romero, Pedro
    [J]. CHEMICAL SOCIETY REVIEWS, 2010, 39 (08) : 3210 - 3239
  • [3] Chemoselective Installation of Diverse Succinimides on Fused Benzimidazoles via Rhodium-Catalyzed C-H Activation/Annulation: Chemosensor for Heavy Metals
    Aslam, Mohammad
    Mohandoss, Sonaimuthu
    Lee, Yong Rok
    [J]. ORGANIC LETTERS, 2021, 23 (16) : 6206 - 6211
  • [4] Ortho-Functionalization of Benzimidates and Benzamidines
    Borah, Gongutri
    Dam, Binoyargha
    Patel, Bhisma K.
    [J]. CHEMISTRYSELECT, 2022, 7 (12):
  • [5] Recent advances in intramolecular C-O/C-N/C-S bond formation via C-H functionalization
    Borpatra, Paran J.
    Deka, Bhaskar
    Deb, Mohit L.
    Baruah, Pranjal K.
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (20) : 3445 - 3489
  • [6] Design of benzimidazole- and benzoxazole-2-thione derivatives as inhibitors of bacterial hyaluronan lyase
    Braun, Stephan
    Botzki, Alexander
    Salmen, Sunnhild
    Textor, Christian
    Bernhardt, Guenther
    Dove, Stefan
    Buschauer, Armin
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2011, 46 (09) : 4419 - 4429
  • [7] Construction of Versatile N-Heterocycles from in situ Generated 1,2-Diaza-1,3-dienes
    Chen, Zhangpei
    Meng, Lingxin
    Ding, Zhiqiang
    Hu, Jianshe
    [J]. CURRENT ORGANIC CHEMISTRY, 2019, 23 (02) : 164 - 187
  • [8] Transition metal-catalyzed C-H bond functionalizations by the use of diverse directing groups
    Chen, Zhengkai
    Wang, Binjie
    Zhang, Jitan
    Yu, Wenlong
    Liu, Zhanxiang
    Zhang, Yuhong
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2015, 2 (09): : 1107 - 1295
  • [9] Transition-Metal-Catalyzed C-H Alkylation Using Alkenes
    Dong, Zhe
    Ren, Zhi
    Thompson, Samuel J.
    Xu, Yan
    Dong, Guangbin
    [J]. CHEMICAL REVIEWS, 2017, 117 (13) : 9333 - 9403
  • [10] Synthesis of Unsaturated N-Heterocycles by Cycloadditions of Aziridines and Alkynes
    Feng, Jian-Jun
    Zhang, Junliang
    [J]. ACS CATALYSIS, 2016, 6 (10): : 6651 - 6661
1234