Rh(III)-Catalyzed Sequential C-H Amination/Annulation Cascade Reactions: Synthesis of Multisubstituted Benzimidazoles

被引:41
|
作者
Huang, Siqi [1 ]
Li, Huan [1 ]
Sun, Xiangying [2 ]
Xu, Linhua [1 ]
Wang, Lianhui [1 ]
Cui, Xiuling [1 ]
机构
[1] Huaqiao Univ, Sch Biomed Sci, Engn Res Ctr Mol Med,Minist Educ, Key Lab Fujian Mol Med,Key Lab Xiamen Marine & Ge, Xiamen 361021, Fujian, Peoples R China
[2] Huaqiao Univ, Sch Mat Sci, Xiamen 361021, Fujian, Peoples R China
关键词
N BOND FORMATION; RHODIUM(III)-CATALYZED SYNTHESIS; CATALYZED DIRECT; 4+2 ANNULATION; O BOND; ACTIVATION; ALKYNES; ACCESS; ANTHRANILS; FACILE;
D O I
10.1021/acs.orglett.9b01902
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient and practical method to construct benzimidazoles via Rh(III)-catalyzed sequential C-H amination and annulation cascade reaction has been developed. The cascade reaction displays high step, atom, and redox economy, is compatible with the air, and has good functional group tolerance and high efficiency. The titled products can be easily further converted into imidazo[4,5-c]acridines, which were observed unique fluorescent properties.
引用
收藏
页码:5570 / 5574
页数:5
相关论文
共 50 条
  • [21] Rh-catalyzed chemo-, stereo- and regioselective C-H cascade annulation of indolyloxopropanenitriles for pyranoindoles
    Kotipalli, Ramesh
    Babu, Undamatla Suri
    Nanubolu, Jagadeesh Babu
    Reddy, Maddi Sridhar
    CHEMICAL COMMUNICATIONS, 2023, 59 (67) : 10137 - 10140
  • [22] Synthesis of Spiropentadiene Pyrazolones by Rh(III)-Catalyzed Formal sp3 C-H Activation/Annulation
    Zheng, Jivan
    Li, Panpan
    Gu, Meng
    Lin, Aijun
    Yao, Hequan
    ORGANIC LETTERS, 2017, 19 (11) : 2829 - 2832
  • [23] Sulfoximines Assisted Rh(III)-Catalyzed C-H Activation/Annulation Cascade to Synthesize Highly Fused Indeno-1,2-benzothiazines
    Li, Jian
    Li, Hui
    Fang, Daqing
    Liu, Lingjun
    Han, Xu
    Sun, Jina
    Li, Chunpu
    Zhou, Yu
    Ye, Deju
    Liu, Hong
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (21) : 15217 - 15227
  • [24] Rh(III)-catalyzed C-H activation/cyclization of oximes with alkenes for regioselective synthesis of isoquinolines
    Chen, Renjie
    Qi, Jifeng
    Mao, Zhenjun
    Cui, Sunliang
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (26) : 6201 - 6204
  • [25] Copper-Catalyzed Radical Methylation/C-H Amination/Oxidation Cascade for the Synthesis of Quinazolinones
    Bao, Yajie
    Yan, Yizhe
    Xu, Kun
    Su, Jihu
    Zha, Zhenggen
    Wang, Zhiyong
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (09) : 4736 - 4742
  • [26] Rh(III)-Catalyzed C-H Annulation of N-Nitrosoanilines with Iodonium Ylides for the Synthesis of N-Alkyl Indoles
    Liu, Chaoshui
    Dai, Qiuzi
    Li, Yaqian
    Huang, Chuhan
    Guo, Lijuan
    Yang, Zi
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (11) : 7281 - 7289
  • [27] Kinetic Control of Rh(III)-Catalyzed Annulation of C-H Bonds with Quinones: Chemoselective Synthesis of Hydrophenanthridinones and Phenanthridinones
    Yang, Wei
    Wang, Jingyi
    Wei, Zhonglin
    Zhang, Qian
    Xu, Xianxiu
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (04) : 1675 - 1680
  • [28] 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
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (08) : 1290 - 1294
  • [29] Intramolecular cascade annulation triggered by rhodium(III)-catalyzed sequential C(sp2) H activation and C(sp3)-H amination
    Song, Liangliang
    Tian, Guilong
    Van der Eycken, Johan
    Van der Eycken, Erik V.
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2019, 15 : 571 - 576
  • [30] Rh(III)-Catalyzed C-H Activation/Cyclization of Indoles and Pyrroles: Divergent Synthesis of Heterocycles
    Zhang, Yan
    Zheng, Jing
    Cui, Sunliang
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (14) : 6490 - 6500