Site-Selective 1,4-Difunctionalization of Nitrogen Heteroaromatics for Constructing Vinylidene Heterocycles

被引:9
|
作者
He, Qianlin [1 ]
Zhong, Mingli [2 ]
Chen, Zhichao [1 ]
Liao, Chuyi [1 ]
Xie, Feng [1 ]
Zhu, Zhongzhi [1 ]
Chen, Xiuwen [1 ]
机构
[1] Wuyi Univ, Sch Biotechnol & Hlth Sci, Jiangmen 529020, Peoples R China
[2] Guilin Med Univ, Coll Pharm, Guilin 541199, Peoples R China
关键词
A one-pot; dearomatization; N-heteroaromatics; difunctionalization; NUCLEOPHILIC DEAROMATIZATION; PYRIDINES; METAL; ARYLATION;
D O I
10.1002/adsc.202101098
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A one-pot protocol for constructing 1,4-difunctionalized quinoline/pyridine derivatives via the reaction of N-heteroaromatics, alkyl halides, and active methylene/methyl compounds was developed. The transformation involves dearomative functionalization of an in situ-activated N-heteroaromatic to construct new C-N and C=C bonds. This reaction has a broad substrate scope and functional group tolerance.
引用
收藏
页码:459 / 463
页数:5
相关论文
共 50 条
  • [41] SITE-SELECTIVE EFFECT OF N-OXIDE FUNCTION TO METHYL-GROUPS ON 6-MEMBERED N-HETEROAROMATICS
    SAKAMOTO, T
    YOSHIZAWA, H
    YAMANAKA, H
    GOTO, Y
    NIIYA, T
    HONJO, N
    HETEROCYCLES, 1982, 17 : 73 - 76
  • [42] Site-Selective Phosphoglycerate Mutase 1 Acetylation by a Small Molecule
    Zhang, Xiaodan
    Jiang, Lulu
    Huang, Ke
    Fang, Chuantao
    Li, Jian
    Yang, Jintong
    Li, Huiti
    Ruan, Xiaoxue
    Wang, Penghui
    Mo, Mingguang
    Wu, Ping
    Xu, Yanhui
    Peng, Chao
    Uesugi, Motonari
    Ye, Deyong
    Yu, Fa-Xing
    Zhou, Lu
    ACS CHEMICAL BIOLOGY, 2020, 15 (03) : 632 - 639
  • [43] Catalyst- and oxidant-free electrooxidative site-selective [3/4+2] annulation to fused polycyclic heteroaromatics
    Guan, Wenjing
    Ying, Ke
    Yuan, Chengcheng
    Hang, Jinlin
    Liu, Chengkou
    Huang, Xiangxing
    Fang, Zheng
    Guo, Kai
    GREEN CHEMISTRY, 2022, 24 (13) : 5191 - 5196
  • [44] Ruthenium-Catalyzed Site-selective Enone Carbonyl Directed ortho-C-H Activation of Aromatics and Heteroaromatics with Alkenes
    Bakthadoss, Manickam
    Kumar, Polu Vijay
    ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (14) : 2650 - 2658
  • [45] Regioselective (site-selective) functionalisation of unsaturated halogenated nitrogen, oxygen and sulfur heterocycles by Pd-catalysed cross-couplings and direct arylation processes
    Fairlamb, Ian J. S.
    CHEMICAL SOCIETY REVIEWS, 2007, 36 (07) : 1036 - 1045
  • [46] Site-Selective Deuteration of N-Heterocycles via Iridium-Catalyzed Hydrogen Isotope Exchange
    Kerr, William J.
    Lindsay, David M.
    Owens, Philippa K.
    Reid, Marc
    Tuttle, Tell
    Campos, Sebastien
    ACS CATALYSIS, 2017, 7 (10): : 7182 - 7186
  • [47] Site-selective and metal-free C–H nitration of biologically relevant N-heterocycles
    Junghyea Moon
    Hyun Ku Ji
    Nayoung Ko
    Harin Oh
    Min Seo Park
    Suho Kim
    Prithwish Ghosh
    Neeraj Kumar Mishra
    In Su Kim
    Archives of Pharmacal Research, 2021, 44 : 1012 - 1023
  • [48] Visible-Light-Induced Site-Selective Difunctionalization of 2,3-Dihydrofuran with Quinoxalin-2(1H)-ones and Peroxides
    Li, Laiqiang
    Gao, Yanhui
    Wang, Lei
    Sun, Mingli
    Liu, Jie
    Li, Pinhua
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 2022 (20)
  • [49] Sequential site-selective C-H activations of aromatic heterocycles through a pH dependent auxiliary
    Daniels, Matthew
    Armand, Jeremy
    Tan, Kian
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 252
  • [50] Site-Selective Benzannulation of Heterocycles in Bidentate Ligands Leads to Blue-Shifted Emission from Dimers
    Mondal, Rajarshi
    Lozada, Issiah B.
    Davis, Rebecca L.
    Williams, J. A. Gareth
    Herbert, David E.
    INORGANIC CHEMISTRY, 2018, 57 (09) : 4966 - 4978