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
  • [21] Site-selective chlorination of pyrrolic heterocycles by flavin dependent enzyme PrnC
    Peh, Guangrong
    Tay, Terence
    Tan, Lee Ling
    Tiong, Elaine
    Bi, Jiawu
    Goh, Yi Ling
    Ye, Suming
    Lin, Fu
    Tan, Cheryl Jia Xin
    Tan, Yong Zi
    Wong, Joel
    Zhao, Huimin
    Wong, Fong Tian
    Ang, Ee Lui
    Lim, Yee Hwee
    COMMUNICATIONS CHEMISTRY, 2024, 7 (01)
  • [22] Dearomative 1,4-difunctionalization of naphthalenes via palladium-catalyzed tandem Heck/Suzuki coupling reaction
    Bo Zhou
    Hongliang Wang
    Zhong-Yan Cao
    Jia-Wen Zhu
    Ren-Xiao Liang
    Xin Hong
    Yi-Xia Jia
    Nature Communications, 11
  • [23] Alkoxyl Radical-Mediated Ring Expansion/1,4-Difunctionalization of 1,3-Enynes upon Copper Catalysis
    Miao, Hong-Jie
    Zhang, Jin-Hua
    Liu, Shuai
    Wang, Wen-Hong
    Yang, Xu
    Duan, Xin-Hua
    Guo, Li-Na
    ORGANIC LETTERS, 2023, 25 (30) : 5563 - 5568
  • [24] Site-Selective Direct γ-Difunctionalization of Diazoenals: Application to the Synthesis of Enal-Functionalized Allenes and Furans
    Kalepu, Jagadeesh
    Sudam Lad, Bapurao
    Kumar Mandal, Pratap
    Kanchupalli, Vinaykumar
    Roy, Durjay
    Katukojvala, Sreenivas
    CHEMISTRY-AN ASIAN JOURNAL, 2025, 20 (01)
  • [25] Photoinduced Decatungstate Anion-Catalyzed 1,4-Difunctionalization of 1,3-Butadienes via C-H Activation
    Ruan, Xiao-Yun
    Wu, Dan-Xing
    Li, Wen-Ao
    Lin, Zihan
    Sayed, Mostafa
    Han, Zhi-Yong
    Gong, Liu-Zhu
    ORGANIC LETTERS, 2024, 26 (26) : 5528 - 5533
  • [26] Copper-Catalyzed Radical 1,4-Difunctionalization of 1,3-Enynes with Alkyl Diacyl Peroxides and N-Fluorobenzenesulfonimide
    Zhu, Xiaotao
    Deng, Weili
    Chiou, Mong-Feng
    Ye, Changqing
    Jian, Wujun
    Zeng, Yuehua
    Jiao, Yihang
    Ge, Liang
    Li, Yajun
    Zhang, Xinhao
    Bao, Hongli
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (01) : 548 - 559
  • [27] A novel synthesis of 3-hydroxypiperidin-2-ones via site-selective difunctionalization of piperidine derivatives
    Wang, Fang
    Zhang, Xinying
    He, Yan
    Fan, Xuesen
    TETRAHEDRON LETTERS, 2019, 60 (42)
  • [28] Constructing low-dimensional phosphorescent MOFs by site-selective coordination engineering
    Zhang, Dan
    Hu, Jingpeng
    Zhu, Yuqi
    Wang, Mengyao
    Liu, Jing
    Li, Hongfeng
    Li, Tianyang
    Liu, Zhongyi
    Li, Jinpeng
    Zhang, Wenlei
    JOURNAL OF MOLECULAR STRUCTURE, 2025, 1334
  • [29] Dearomative 1,4-Difunctionalization of Non-Activated Arenes Enabled by Boryl Radical-Mediated Halogen-Atom Transfer
    Deng, Congling
    Wu, Hao
    Li, Sheng
    Chen, Li
    Liu, Xiaozu
    Liu, Peijun
    ACS CATALYSIS, 2025, 15 (02): : 1294 - 1304
  • [30] Site-selective and Stereoselective Syntheses Controlled by the Electron-withdrawing Properties of Cationic Heterocycles
    Nishikawa, Yasuhiro
    YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, 2020, 140 (10): : 1225 - 1233