Construction of Vinyl-Substituted N-Heterocycles via Rh(III)- Catalyzed C-H Functionalization/Annulation of Pyrazolidinones

被引:12
作者
Zhang, Shurui [1 ,2 ]
Hu, Shulei [3 ,4 ]
Wang, Kean [5 ]
Yang, Zhao [3 ]
Liu, Hong [2 ,3 ,4 ,5 ]
Wang, Jiang [1 ,4 ]
机构
[1] Lingang Lab, Shanghai 200031, Peoples R China
[2] ShanghaiTech Univ, Sch Life Sci & Technol, Shanghai 200031, Peoples R China
[3] China Pharmaceut Univ, 639 Longmian Ave, Nanjing 211198, Peoples R China
[4] Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, 555 Zu Chong Zhi Rd, Shanghai 201203, Peoples R China
[5] Nanjing Univ Chinese Med, Sch Chinese Mat Med, Nanjing 210023, Peoples R China
基金
中国国家自然科学基金;
关键词
annulation reactions; C-H activation; pyrazolidinone; Rh(III)-catalyzed; DIRECTING-GROUP; CYCLOADDITIONS; CINNOLINES; ALKYNES; ARENES;
D O I
10.1002/adsc.202201065
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
The transition-metal-catalyzed C-H activation and annulation reactions of pyrazolidinones with 4-vinyl-1,3-dioxolan-2-one or vinylene carbonate are described herein. This protocol provided two types of pyrazolo[1,2-a]cinnolines as essential assets for the development of bioactive compounds, and the synthetic practicality was performed and explained with 44 examples. The possible mechanism of these two reactions is proposed based on preliminary studies and previous reports, and no oxidant was added to both reactions.
引用
收藏
页码:238 / 243
页数:6
相关论文
共 50 条
  • [11] Practical synthesis of isocoumarins via Rh(III)-catalyzed C-H activation/annulation cascade
    Gao, Qian-Ci
    Li, Yi-Fei
    Xuan, Jun
    Hu, Xiao-Qiang
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2023, 19 : 100 - 106
  • [12] Palladium-Catalyzed C-H Allylation/Annulation Reaction of Amides and Allylic Alcohols: Regioselective Construction of Vinyl-Substituted 3,4-Dihydroisoquinolones
    Wu, Haijian
    Gui, Jing
    Sun, Manman
    Ma, Yongmin
    Yang, Jianguo
    Wang, Zhiming
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (06) : 3871 - 3882
  • [13] Divergent C-H Annulation for Multifused N-Heterocycles: Regio- and Stereospecific Cyclizations of N-Alkynylindoles
    Alam, Khyarul
    Hong, Sung Won
    Oh, Kyung Hwan
    Park, Jin Kyoon
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (43) : 13387 - 13391
  • [14] Direct Integration of Phthalazinone and Succinimide Scaffolds via Rh(III)-Catalyzed C-H Functionalization
    Sun Cho, Yong
    Do Kim, Hak
    Kim, Euntaek
    Hoon Han, Sang
    Bong Han, Soo
    Kumar Mishra, Neeraj
    Hoon Jung, Young
    Jeong, Taejoo
    Su Kim, In
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 10 (01) : 202 - 209
  • [15] Asymmetric Synthesis of α-Branched Amines via Rh(III)-Catalyzed C-H Bond Functionalization
    Wangweerawong, Apiwat
    Bergman, Robert G.
    Ellman, Jonathan A.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (24) : 8520 - 8523
  • [16] Quinazoline Synthesis via Rh(III)-Catalyzed Intermolecular C-H Functionalization of Benzimidates with Dioxazolones
    Wang, Jie
    Zha, Shanke
    Chen, Kehao
    Zhang, Feifei
    Song, Chao
    Zhu, Jin
    ORGANIC LETTERS, 2016, 18 (09) : 2062 - 2065
  • [17] Synthesis of isoquinolinone derivatives by Rh (III)-catalyzed C-H functionalization of N-ethoxybenzamides
    Chen Junyu
    Zhang Lei
    Zheng Xiangyun
    Zhou Jian
    Zhong Tianshuo
    Yu Chuanming
    SYNTHETIC COMMUNICATIONS, 2020, 50 (12) : 1799 - 1812
  • [18] Rh(III)-catalyzed aromatic C-H bond carbenoid functionalization of triazenes by α-diazomalonate
    Wang, Dahai
    Cui, Sunliang
    TETRAHEDRON, 2016, 72 (22) : 2725 - 2730
  • [19] Rh(III)-catalyzed aldehyde C-H bond functionalization of salicylaldehydes with arylboronic acids
    Wang, Dahai
    Cui, Sunliang
    TETRAHEDRON, 2015, 71 (45) : 8511 - 8516
  • [20] Synthesis of fused N-heterocycles via tandem C-H activation
    Meng, Ge
    Niu, Hong-Ying
    Qu, Gui-Rong
    Fossey, John S.
    Li, Jian-Ping
    Guo, Hai-Ming
    CHEMICAL COMMUNICATIONS, 2012, 48 (77) : 9601 - 9603