Regioselective Synthesis of Benzimidazolones via Cascade C-N Coupling of Monosubstituted Ureas

被引：25
|
作者：
Ernst, Johannes B. [1 ]
Tay, Nicholas E. S. [1 ]
Jui, Nathan T. [1 ]
Buchwald, Stephen L. [1 ]
机构：
[1] MIT, Dept Chem, Cambridge, MA 02139 USA
来源：
ORGANIC LETTERS | 2014年 / 16卷 / 14期
基金：
美国国家卫生研究院;
关键词：
CATALYZED INTRAMOLECULAR CYCLIZATION; SUBSTITUTED 1,3-DIHYDROBENZIMIDAZOL-2-ONES; INHIBITORS; SERIES; HETEROCYCLES; DERIVATIVES; ANTAGONIST; AMINATION; DISCOVERY; ARYLATION;
D O I：
10.1021/ol501531q
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A direct method for the regioselective construction of benzimidazolones is reported wherein a single palladium catalyst is employed to couple monosubstituted urea substrates with differentially substituted 1,2-dihaloaromatic systems. In this method, the catalyst is able to promote a cascade of two discrete chemoselective C-N bond-forming processes that allows the highly selective and predictable formation of complex heterocycles from simple, readily available starting materials.
引用
收藏
页码：3844 / 3846
页数：3
相关论文
共 50 条
  • [1] Catalyst-Free Electrosynthesis of Benzimidazolones through Intramolecular Oxidative C-N Coupling
    Li, Jiang-Sheng
    Yang, Pan-Pan
    Xie, Xin-Yun
    Jiang, Si
    Tao, Li
    Li, Zhi-Wei
    Lu, Cui-Hong
    Liu, Wei-Dong
    ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (10) : 1977 - 1981
  • [2] Efficient and Regioselective Synthesis of Phenothiazine via Ferric Citrate Catalyzed C-S/C-N Cross-Coupling
    Das, Tonmoy Chitta
    Quadri, Syed Aziz Imam
    Farooqui, Mazahar
    LETTERS IN ORGANIC CHEMISTRY, 2019, 16 (01) : 16 - 24
  • [3] Synthesis of Macrocyclic Aromatic Amines via C-N Coupling Reaction
    Tsuchiya, Kousuke
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2011, 69 (02) : 169 - 170
  • [4] Synthesis of C-N or C-C Spiroindolines via Rearrangement Coupling Reaction
    Liu, Xiaoling
    Qiao, Panpan
    Chen, Hui
    Gao, Yu
    Chen, Haijun
    ORGANIC LETTERS, 2024, 26 (45) : 9759 - 9763
  • [5] Recent advances in electrochemical synthesis of urea via C-N coupling
    Wang, Chen
    Gao, Wenqi
    Hu, Wei
    Wen, Wei
    Wang, Shengfu
    Zhang, Xiuhua
    Yan, Dafeng
    Xia, Bao Yu
    JOURNAL OF ENERGY CHEMISTRY, 2024, 98 : 294 - 310
  • [6] Organoiodine Catalysed Intramolecular C-N Bond Oxidative Coupling for the Synthesis of 3-Monosubstituted Oxindoles
    Yu, Jiang-Ning
    Wang, Yue
    Yin, Ji-Chen
    Wang, Yang
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 27 (46)
  • [7] A tandem and tunable Pd catalyzed C-N coupling of heteroarenols with ureas via C-OH bond activation
    Dalvadi, Jignesh P.
    Patel, Poojan K.
    Chikhalia, Kishor H.
    TETRAHEDRON, 2014, 70 (49) : 9394 - 9404
  • [8] An economical approach for peptide synthesis via regioselective C-N bond cleavage of lactams
    Muramatsu, Wataru
    Yamamoto, Hisashi
    CHEMICAL SCIENCE, 2022, 13 (21) : 6309 - 6315
  • [9] Regioselective C-N bond formation via gold catalysis
    Marchetti, Louis
    Kantak, Abhishek
    Davis, Riley
    DeBoef, Brenton
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2015, 250
  • [10] Synthesis of unsymmetrical 1,3-substituted-1,3-dihydro-benzimidazolones via copper-catalyzed C-N coupling under visible light
    Liu, Jianjun
    Zuo, Shengli
    Huang, Jieying
    Zhang, Fan
    Zuo, Ang
    NEW JOURNAL OF CHEMISTRY, 2022, 46 (26) : 12465 - 12469
12345