Cobalt-Catalyzed Cycloamination: Synthesis and Photophysical Properties of Polycyclic N-Heterocycles

被引:32
|
作者
Dong, Yu [1 ,2 ]
Yang, Jian [1 ,2 ]
Zhang, Hua [1 ,2 ]
Zhan, Xiao-Yu [1 ,2 ]
He, Shuai [3 ]
Shi, Zhi-Chuan [3 ]
Zhang, Xiao-Mei [1 ]
Wang, Ji-Yu [1 ]
机构
[1] Chinese Acad Sci, Chengdu Inst Organ Chem, Chengdu 610041, Peoples R China
[2] Univ Chinese Acad Sci, Beijing 100049, Peoples R China
[3] Southwest Minzu Univ, Chengdu 610041, Peoples R China
关键词
C-H AMINATION; ACID; DERIVATIVES; CARBAZOLES; ANILINES; ACCESS;
D O I
10.1021/acs.orglett.0c01753
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first earth-abundant cobalt-catalyzed cycloamination of indolylquinones and various (hetero)aromatic amine under ligand-free conditions for the synthesis of polycyclic N-heterocycles has been developed. The process allows facile access to polycyclic N-heterocycles with tolerance of chloride, bromide, amino, thio, etc. groups in moderate to high yields (up to 89%). In addition, The photophysical properties of the synthesized products were evaluated. These products exhibit interesting fluorescence properties, which is promising for fluorescent probes.
引用
收藏
页码:5151 / 5156
页数:6
相关论文
共 50 条
  • [41] 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)
  • [42] Vanadium-Catalyzed Dehydrogenation of N-Heterocycles in Water
    Zumbraegel, Nadine
    Sako, Makoto
    Takizawa, Shinobu
    Sasai, Hiroaki
    Groeger, Harald
    ORGANIC LETTERS, 2018, 20 (16) : 4723 - 4727
  • [43] Cp*Rh(III)-Catalyzed Divergent Synthesis of N-Heterocycles with N-Methoxyindoleamides and Isoxazolones
    Shen, Dan-Ting
    Zou, Wen-Xuan
    Chen, Shao-Yong
    Xiao, Lin
    Hu, Qiong
    Song, Jia-Lin
    Liu, Xu-Ge
    Zhang, Shang-Shi
    ADVANCED SYNTHESIS & CATALYSIS, 2024, 366 (19) : 4089 - 4094
  • [44] Zinc-Catalyzed Hydrosilylation and Hydroboration of N-Heterocycles
    Lortie, John L.
    Dudding, Travis
    Gabidullin, Bulat M.
    Nikonov, Georgii I.
    ACS CATALYSIS, 2017, 7 (12): : 8454 - 8459
  • [45] Cu(I) Complexes Catalyzed the Dehydrogenation of N-Heterocycles
    Shen, Yangyang
    Chen, Fei
    Du, Zhihong
    Zhang, Hao
    Liu, Jichang
    Liu, Ning
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (07): : 4530 - 4537
  • [46] Pd/Ag-Cocatalyzed Merging Intramolecular Oxidative Coupling and Cascade [4+2] Cycloaddition: Synthesis and Photophysical Properties of Novel Polycyclic N-Heterocycles Fused Naphthoquinones
    Dong, Yu
    Chen, Lin
    Wu, Han-Qing
    Xie, Li
    Yu, Jing-Hao
    Yang, Fan
    Wang, Yu-Ting
    Liu, Yu-Rong
    Deng, Guo-Wei
    Wang, Zhi-Fan
    MOLECULES, 2024, 29 (23):
  • [47] Cobalt-Catalyzed Cycloisomerization of N,N-Diallylanilines
    Liu, Jun
    Yang, Zhanhui
    Zheng, Minfang
    Wu, Hongfei
    Chen, Ning
    Xu, Jiaxi
    SYNTHESIS-STUTTGART, 2019, 51 (17): : 3320 - 3326
  • [48] Insights on the Synthesis of N-Heterocycles Containing Macrocycles and Their Complexion and Biological Properties
    Malek, Fouad
    Harit, Tarik
    Cherfi, Mounir
    Kim, Bonglee
    MOLECULES, 2022, 27 (07):
  • [49] Synthesis of chiral polycyclic N-heterocycles via gold(i)-catalyzed 1,6-enyne cyclization/intramolecular nucleophilic addition
    Han, Xu
    Gaignard-Gaillard, Quentin
    Retailleau, Pascal
    Gandon, Vincent
    Voituriez, Arnaud
    CHEMICAL COMMUNICATIONS, 2022, 58 (18) : 3043 - 3046
  • [50] Synthesis of Spiro Polycyclic N-Heterocycles and Indolecarbazoles via Merging Oxidative Coupling and Cascade Palladium-Catalyzed Intramolecular Oxidative Cyclization
    Dong, Yu
    Lan, Mei-Feng
    Lin, Yue-Qin
    Chen, Lin
    Wu, Chun-Mei
    Wang, Zhi-Fan
    Shi, Zhi-Chuan
    Deng, Guo-wei
    He, Bing
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (09): : 6474 - 6488