Synthesis of Poly-Substituted Pyridines via Noble-Metal-Free Cycloaddition of Ketones and Imines

被引:1
|
作者
Mao, Yeting [1 ]
Mao, Hong [1 ]
Xu, Jiaojiao [1 ]
Liu, Tianqi [1 ]
Liu, Bingxin [1 ]
Tan, Qitao [1 ]
Ding, Chang-Hua [1 ]
Xu, Bin [1 ,2 ]
机构
[1] Shanghai Univ, Affiliated Nantong Hosp, Shanghai Engn Res Ctr Organ Repair,Dept Chem, Innovat Drug Res Ctr,Peoples Hosp Nantong 6, Shanghai 200444, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
基金
中国国家自然科学基金;
关键词
substituted pyridine; formal [4+2] cycloaddition; ketone; imine; noble-metal-free; HIGHLY FUNCTIONALIZED PYRIDINES; BOND-CLEAVAGE; ALPHA; BETA-UNSATURATED KETOXIMES; REGIOSELECTIVE SYNTHESIS; CATALYZED CYCLIZATION; TERMINAL ALKYNES; OXIMES; CONSTRUCTION; ISOCYANIDES; INHIBITORS;
D O I
10.1002/asia.202100983
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An eco-friendly and noble-metal-free formal [4+2] cycloaddition reaction was developed for the efficient synthesis of biologically interesting poly-substituted pyridines from easily available ketones and imines, whereby two sequential C-C bonds are formed. The given approach features a unique synthetic strategy of imines and ketones with wide substrate scope, good functional group tolerance, mild conditions and operational simplicity, which represents a more direct pathway to synthesize poly-substituted pyridines than traditional methods.
引用
收藏
页码:3905 / 3908
页数:4
相关论文
共 50 条
  • [21] Regulable cross-coupling of alcohols and benzothiazoles via a noble-metal-free photocatalyst under visible light
    Pan, Zi-Tong
    Qi, Xu-Kuan
    Xiao, Qian
    Liang, Xi-Wen
    Zhong, Jian-Ji
    Jian, Jing-Xin
    Tong, Qing-Xiao
    CHEMICAL COMMUNICATIONS, 2022, 58 (63) : 8810 - 8813
  • [22] An expedient synthesis of poly-substituted pyrroles from γ-ketonitriles via indium-mediated Barbier reaction strategy
    Kim, Sung Hwan
    Kim, Se Hee
    Lee, Ka Young
    Kim, Jae Nyoung
    TETRAHEDRON LETTERS, 2009, 50 (41) : 5744 - 5747
  • [23] A Facile Synthesis of Noble-Metal-Free Catalyst Based on Nitrogen Doped Graphene Oxide for Oxygen Reduction Reaction
    Vasiliev, Vladimir P.
    Manzhos, Roman A.
    Kochergin, Valeriy K.
    Krivenko, Alexander G.
    Kabachkov, Eugene N.
    Kulikov, Alexander V.
    Shulga, Yury M.
    Gutsev, Gennady L.
    MATERIALS, 2022, 15 (03)
  • [24] Synthesis of di- and poly-substituted phenols via [4+2] type cyclo-condensation
    Shao, Ming-Zhe
    Liu, Xiao-Yu
    Li, Fang-Qing
    Chen, Zili
    TETRAHEDRON LETTERS, 2021, 71
  • [25] Nickel oxide nanoparticles catalyzed synthesis of poly-substituted quinolines via Friedlander hetero-annulation reaction
    Reddy, B. Palakshi
    Iniyavan, P.
    Sarveswari, S.
    Vijayakumar, V.
    CHINESE CHEMICAL LETTERS, 2014, 25 (12) : 1595 - 1600
  • [26] Nickel oxide nanoparticles catalyzed synthesis of poly-substituted quinolines via Friedlander hetero-annulation reaction
    B.Palakshi Reddy
    P.Iniyavan
    S.Sarveswari
    V.Vijayakumar
    Chinese Chemical Letters, 2014, 25 (12) : 1595 - 1600
  • [27] Transition-Metal-Free Synthesis of Substituted Pyridines via Ring Expansion of 2-Allyl-2H-azirines
    Jiang, Yaojia
    Park, Cheol-Min
    Loh, Teck-Peng
    ORGANIC LETTERS, 2014, 16 (13) : 3432 - 3435
  • [28] Metal-Free and Regioselective Synthesis of Substituted and Fused Chromenopyrrole Scaffolds via the Divergent Reactivity of α-Azido Ketones in Water
    Dhanasekar, Elumalai
    Kannan, Tharanikkarasu
    Venkatesan, Rengarajan
    Perumal, Paramasivam Thirumalai
    Kamalraja, Jayabal
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (15): : 9631 - 9649
  • [29] Enhancing CO2 photoreduction via the perfluorination of Co(II) phthalocyanine catalysts in a noble-metal-free system
    Li, Zizi
    Wang, Jia-Wei
    Huang, Yanjun
    Ouyang, Gangfeng
    CHINESE JOURNAL OF CATALYSIS, 2023, 49 : 160 - 167
  • [30] A New Strategy for the Synthesis of Poly-Substituted 3-H, 3-Fluoro, or 3-Trifluoromethyl Pyridines via the Tandem C-F Bond Cleavage Protocol
    Chen, Zixian
    Zhu, Jiangtao
    Xie, Haibo
    Li, Shan
    Wu, Yongming
    Gong, Yuefa
    ORGANIC LETTERS, 2010, 12 (19) : 4376 - 4379