Access to cyano-substituted pyrazolines through copper-catalyzed cascade cyanation/cyclization of unactivated olefins

被引：15
|
作者：
Meng, Fei [1 ,2 ]
Fang, Qin [1 ,2 ]
Yuan, Weidong [1 ,2 ]
Xu, Ning [1 ,2 ]
Cao, Shujun [1 ,2 ]
Chun, Jianlin [1 ,2 ]
Li, Jie [1 ,2 ]
Zhang, Honglin [1 ,2 ]
Zhu, Yingguang [1 ,2 ]
机构：
[1] Nanjing Agr Univ, Jiangsu Key Lab Pesticide Sci, Coll Sci, Nanjing 210095, Peoples R China
[2] Nanjing Agr Univ, Dept Chem, Coll Sci, Nanjing 210095, Peoples R China
来源：
ORGANIC CHEMISTRY FRONTIERS | 2020年 / 7卷 / 11期
基金：
中国国家自然科学基金;
关键词：
C-H CYANATION; N-RADICAL CASCADE; INTRAMOLECULAR AMINOCYANATION; OXIDATIVE CYANATION; ALKENES SYNTHESIS; BOND FORMATION; ARENES; DIFUNCTIONALIZATION; DIAMINATION; PALLADIUM;
D O I：
10.1039/d0qo00282h
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A novel and efficient copper-catalyzed domino cyanation/cyclization of hydrazone-tethered unactivated olefins has been developed. A range of cyano-containing pyrazolines have been easily obtained in good yields under mild conditions. This method provides a facile, practical, and rapid access to valuable pyrazolines with the important cyano functionality, and it is amenable for gram scale synthesis. The simultaneous formation of C(sp(3))-CN and C-N bonds can be achieved in a single step.
引用
收藏
页码：1358 / 1364
页数：7
相关论文
共 50 条
  • [21] Copper-catalyzed synthesis of quinazolines via cascade cyclization/hydrodehalogenation
    Ma, Peng
    Wang, Yuhang
    Wang, Jianhui
    Ma, Ning
    NEW JOURNAL OF CHEMISTRY, 2023, 47 (19) : 9377 - 9382
  • [22] Copper-catalyzed radical cascade cyclization for the synthesis of phosphorated indolines
    Zhang, Hong-Yu
    Mao, Liu-Liang
    Yang, Bin
    Yang, Shang-Dong
    CHEMICAL COMMUNICATIONS, 2015, 51 (19) : 4101 - 4104
  • [23] Access to functionalized pyrrolidones via copper-catalyzed aminooxygenation of unactivated alkenes
    Rao, Wei-Hao
    Jiang, Li-Li
    Chen, Fang-Yuan
    Zhang, Meng
    Guo, Yi-Yuan
    Chen, Jia-Jia
    Cui, Ying
    Zou, Guo-Dong
    Tang, Lin
    TETRAHEDRON LETTERS, 2020, 61 (09)
  • [24] Copper-Catalyzed 1,2-Aminocyanation of Unactivated Alkenes via Cyano Migration
    Kwon, Yungeun
    Wang, Qiu
    ORGANIC LETTERS, 2020, 22 (11) : 4141 - 4145
  • [25] Regioselective access to polycyclic N-heterocycles via homogeneous copper-catalyzed cascade cyclization of allenynes
    Kua-Fei Wei
    Qing Liu
    Guang Ma
    Xiao-Lei Jiang
    Xiu-Hong Zhu
    Guang-Xin Ru
    Wen-Bo Shen
    Communications Chemistry, 6
  • [26] Regioselective access to polycyclic N-heterocycles via homogeneous copper-catalyzed cascade cyclization of allenynes
    Wei, Kua-Fei
    Liu, Qing
    Ma, Guang
    Jiang, Xiao-Lei
    Zhu, Xiu-Hong
    Ru, Guang-Xin
    Shen, Wen-Bo
    COMMUNICATIONS CHEMISTRY, 2023, 6 (01)
  • [27] Divergent Syntheses of 2-Aminonicotinonitriles and Pyrazolines by Copper-Catalyzed Cyclization of Oxime Ester
    Wu, Qifan
    Zhang, Yan
    Cui, Sunliang
    ORGANIC LETTERS, 2014, 16 (05) : 1350 - 1353
  • [28] Directed copper-catalyzed C-H functionalization of unactivated olefins with azodicarbonamide compounds
    Cui, Jing
    Wang, Xiaoya
    Zeng, Runsheng
    RSC ADVANCES, 2024, 14 (38) : 27475 - 27480
  • [29] Copper-catalyzed cascade radical cyclization of alkynoates: construction of aryldifluoromethylated coumarins
    Zeng, Piaopiao
    Huang, Xiaoxiao
    Tang, Wei
    Chen, Zhiwei
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (46) : 10223 - 10227
  • [30] Copper-Catalyzed Decarboxylative Cascade Cyclization for the Synthesis of 2-Arylquinolines
    Chatterjee, Rana
    Pothireddy, Mohanreddy
    Dandela, Rambabu
    SYNLETT, 2023, 34 (09) : 1058 - 1062
12345