Rh(III)-catalyzed C-H activation/cyclization of oximes with alkenes for regioselective synthesis of isoquinolines

被引：35
|
作者：
Chen, Renjie [1 ]
Qi, Jifeng [1 ]
Mao, Zhenjun [1 ]
Cui, Sunliang [1 ]
机构：
[1] Zhejiang Univ, Inst Drug Discovery & Design, Coll Pharmaceut Sci, Hangzhou 310058, Zhejiang, Peoples R China
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2016年 / 14卷 / 26期
基金：
中国国家自然科学基金;
关键词：
N BOND FORMATION; BETA-PHENYLETHYLAMINES; INTERNAL ALKYNES; FACILE SYNTHESIS; ACTIVATION; ACCESS; ACIDS; ANNULATION; BENZAMIDES; ALKALOIDS;
D O I：
10.1039/c6ob00942e
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A Rh(III)-catalyzed C-H activation/cyclization of oximes and alkenes for facile and regioselective access to isoquinolines has been developed. This protocol features mild reaction conditions and easily accessible starting materials, and has been applied to the concise synthesis of moxaverine. A kinetic isotope effect study was conducted and a plausible mechanism was proposed.
引用
收藏
页码：6201 / 6204
页数：4
相关论文
共 50 条
  • [1] Synthesis of Isoquinolines via Rh(III)-Catalyzed C-H Activation Using Hydrazone as a New Oxidizing Directing Group
    Chuang, Sheng-Chieh
    Gandeepan, Parthasarathy
    Cheng, Chien-Hong
    ORGANIC LETTERS, 2013, 15 (22) : 5750 - 5753
  • [2] 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
  • [3] Synthesis of Mesoionic Isoquinolines by Rhodium(III)-Catalyzed C-H Activation
    Zhang, Wei
    Wang, Cheng-Qi
    Lin, Hui
    Dong, Lin
    Xu, Yan-Jun
    CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (03) : 907 - 910
  • [4] Rh(III)-Catalyzed C-H Activation/Cyclization of Benzamides and Diazonaphthalen-2(1H)-ones for Synthesis of Lactones
    Chen, Renjie
    Cui, Sunliang
    ORGANIC LETTERS, 2017, 19 (15) : 4002 - 4005
  • [5] Ru-catalyzed C-H activation/cyclization of oximes with sulfoxonium ylides to access isoquinolines
    Yang, Darun
    Xu, Hongyan
    Zhang, Xuejun
    Hu, Yuntao
    Huang, Decai
    Zhao, Huaiqing
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (33) : 6750 - 6756
  • [6] Rh(III)-Catalyzed intramolecular redox-neutral cyclization of alkenes via C-H activation
    Shi, Zhuangzhi
    Boultadakis-Arapinis, Melissa
    Koester, Dennis C.
    Glorius, Frank
    CHEMICAL COMMUNICATIONS, 2014, 50 (20) : 2650 - 2652
  • [7] Rh(III)-Catalyzed C-H Activation and Double Directing Group Strategy for the Regioselective Synthesis of Naphthyridinones
    Huckins, John R.
    Bercot, Eric A.
    Thiel, Oliver R.
    Hwang, Tsang-Lin
    Bio, Matthew M.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (39) : 14492 - 14495
  • [8] Ligand design for Rh(III)-catalyzed C-H activation: an unsymmetrical cyclopentadienyl group enables a regioselective synthesis of dihydroisoquinolones
    Hyster, Todd K.
    Dalton, Derek M.
    Rovis, Tomislav
    CHEMICAL SCIENCE, 2015, 6 (01) : 254 - 258
  • [9] Palladium-Catalyzed C-H Functionalization of Aromatic Oximes: A Strategy for the Synthesis of Isoquinolines
    Zhu, Zhongzhi
    Tang, Xiaodong
    Li, Xianwei
    Wu, Wanqing
    Deng, Guohua
    Jiang, Huanfeng
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (04): : 1401 - 1409
  • [10] The synthesis of spirocyclopropane skeletons enabled by Rh(III)-catalyzed enantioselective C-H activation/[4
    Wang, Hao
    Li, Yidi
    Huang, Lin
    Xu, Huiying
    Jiao, Yukun
    Zhou, Zhi
    Tang, Zhenhao
    Fang, Feifei
    Zhang, Xiaoxue
    Ding, Kan
    Yi, Wei
    Liu, Hong
    Wu, Xiaowei
    Zhou, Yu
    CHEM CATALYSIS, 2023, 3 (12):
12345