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
  • [1] Assembly of polycyclic N-heterocycles via copper-catalyzed cycloamination of indolylquinones and aromatic amines
    Dong, Yu
    Mei, Ting
    Ye, Ji-Xian
    Chen, Xiang-Long
    Jiang, Hui
    Chang, Bo
    Wang, Zhi-Fan
    Shi, Zhi-Chuan
    Li, Zhong-Hui
    He, Bing
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (20) : 4593 - 4598
  • [2] Cycloamination strategies for renewable N-heterocycles
    Li, Hu
    Guo, Haixin
    Fang, Zhen
    Aida, Taku Michael
    Smith, Richard Lee, Jr.
    GREEN CHEMISTRY, 2020, 22 (03) : 582 - 611
  • [3] Cobalt-Catalyzed Synthesis of Functionalized Nordazepams and Benzimidazoquinazolines and Their Photophysical Properties
    Suresh, Sundararajan
    Keerthana, Pari
    Khan, Fazlurrahman Nawaz
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2025, 14 (01)
  • [4] Cobalt Nanoparticles Catalyzed N-Heterocycles Synthesis via Acceptorless Dehydrogenative Coupling
    Ren, Changyue
    Chen, Shuiyan
    Yuan, Zeli
    Fu, Rui
    Cui, Yanbin
    Ma, Zhuang
    Li, Weizuo
    Li, Xinmin
    CHEMISTRY-A EUROPEAN JOURNAL, 2024, 30 (56)
  • [5] Cobalt-Catalyzed Cascade Reaction of Ynamides and 1,3-Dicarbonyl Compounds for Selective Synthesis of Differently Sized N-Heterocycles
    Zhang, Biao
    Yang, Xu-Heng
    Huang, Jian
    Tao, Cheng-an
    Wang, Jianfang
    ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (05) : 753 - 759
  • [6] Recent Advances in the High-Valent Cobalt-Catalyzed C-H Functionalization of N-Heterocycles
    Chandra, Devesh
    Manisha
    Sharma, Upendra
    CHEMICAL RECORD, 2022, 22 (03):
  • [7] Titanium catalyzed synthesis of amines and N-heterocycles
    Schafer, Laurel L.
    Manssen, Manfred
    Edwards, Peter M.
    Lui, Erica K. J.
    Griffin, Samuel E.
    Dunbar, Christine R.
    ADVANCES IN ORGANOMETALLIC CHEMISTRY, VOL 74, 2020, 74 : 405 - 468
  • [8] Cobalt-catalyzed conformationally restricted alkylarylation enables divergent access to Csp3-rich N-heterocycles
    Chen, Kaixin
    Lin, Jie
    Jing, Jing
    Wang, Junda
    Hu, Jiayu
    Yi, Hong
    Lei, Aiwen
    Li, Jie
    CHEMICAL SCIENCE, 2024, 15 (39) : 16250 - 16258
  • [9] Aerobic oxidative dehydrogenation of N-heterocycles catalyzed by cobalt porphyrin
    Zhou, Weiyou
    Chen, Dongwei
    Sun, Fu'an
    Qian, Junfeng
    He, Mingyang
    Chen, Qun
    TETRAHEDRON LETTERS, 2018, 59 (10) : 949 - 953
  • [10] Cobalt(II) Porphyrin-Catalyzed Intramolecular Cyclopropanation of N-Alkyl Indoles/Pyrroles with Alkylcarbene: Efficient Synthesis of Polycyclic N-Heterocycles
    Reddy, Annapureddy Rajasekar
    Hao, Fei
    Wu, Kai
    Zhou, Cong-Ying
    Che, Chi-Ming
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (05) : 1810 - 1815