Synthesis of Imidazo[1,5-a]quinolines via Metal-Free Oxidative Amination of sp3 C-H Bonds

被引：10
|
作者：
Liu, Huanhuan [1 ]
Wang, Xinfeng [1 ]
Ma, Chen [1 ,2 ]
机构：
[1] Shandong Univ, Sch Chem & Chem Engn, Jinan 250100, Shandong, Peoples R China
[2] Peking Univ, State Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R China
来源：
SYNTHESIS-STUTTGART | 2018年 / 50卷 / 14期
基金：
中国国家自然科学基金;
关键词：
quinolone; amino acid; metal-free; oxidative amination; C-H functionalization; EFFICIENT SYNTHESIS; HIGHLY POTENT; DERIVATIVES; LIGANDS; DESIGN; AMINES;
D O I：
10.1055/s-0037-1610137
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A novel oxidative amination of sp(3) C-H bonds was developed for the efficient synthesis of imidazo[1,5-a]quinolines from readily available -amino acids and (2-azaaryl)methanes. This domino protocol, which was established in a TBAI-TBHP oxidation system, includes transition-metal-free decarboxylation and intramolecular cyclization. This method represented a new avenue for the synthesis of N-heterocycles using 2-methylquinolines as the synthon of quinoline-2-carbaldehydes.
引用
收藏
页码：2761 / 2767
页数：7
相关论文
共 50 条
  • [41] Primary amination of C(sp3)–H bonds
    Jan-Stefan Völler
    Nature Catalysis, 2020, 3 : 473 - 473
  • [42] DDQ-mediated direct oxidative coupling of amides with benzylic and allylic sp3 C-H bonds under metal-free conditions
    Ramesh, D.
    Ramulu, U.
    Mukkanti, K.
    Venkateswarlu, Y.
    TETRAHEDRON LETTERS, 2012, 53 (23) : 2904 - 2908
  • [43] Metal-free cascade construction of C-C bonds by activation of inert C(sp3)-H bonds
    Zhang, Honglin
    Pan, Changduo
    Jin, Ning
    Gu, Zhangxi
    Hu, Hongwen
    Zhu, Chengjian
    CHEMICAL COMMUNICATIONS, 2015, 51 (07) : 1320 - 1322
  • [44] Transition Metal-Free sp3 C-H Functionalization of Arylacetic Acids for the Synthesis of 1,3,5-Triazines
    Pardeshi, Sachin D.
    Sathe, Pratima A.
    Pawar, Balu V.
    Vadagaonkar, Kamlesh S.
    Chaskar, Atul C.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (18) : 2098 - 2102
  • [45] An Efficient Metal-Free Oxidative Esterification and Amination of Benzyl C-H Bond
    Liu, Saiwen
    Chen, Ru
    He, Guowen
    Zhang, Jin
    MOLECULES, 2020, 25 (07):
  • [46] Electrochemical dual oxidative C(sp3)-H amination: switchable synthesis of imidazo-fused quinazolinones
    Du, Chengbin
    Zhang, Yan
    Li, Tong
    Zha, Zhenggen
    Wang, Zhiyong
    CHEMICAL COMMUNICATIONS, 2024, 60 (40) : 5274 - 5277
  • [47] Metal-free, organocatalytic cascade formation of C-N and C-O bonds through dual sp3 C-H activation: oxidative synthesis of oxazole derivatives
    Xie, Jin
    Jiang, Honglai
    Cheng, Yixiang
    Zhu, Chengjian
    CHEMICAL COMMUNICATIONS, 2012, 48 (07) : 979 - 981
  • [48] Metal-free direct alkylation of unfunctionalized allylic/benzylic sp3 C-H bonds via photoredox induced radical cation deprotonation
    Zhou, Rong
    Liu, Haiwang
    Tao, Hairong
    Yu, Xingjian
    Wu, Jie
    CHEMICAL SCIENCE, 2017, 8 (06) : 4654 - 4659
  • [49] Metal-free polyporphyrin based photocatalysts for the functionalization of C(sp3)-H bonds in water
    Sun, Xinhao
    Zheng, Nan
    Liu, Gongbo
    Wu, Qiming
    Song, Wangze
    CHEMICAL COMMUNICATIONS, 2022, 58 (95) : 13234 - 13237
  • [50] Synthesis of Fused Imidazole-Containing Ring Systems via Dual Oxidative Amination of C(sp3)-H Bonds
    Castanedo, Georgette
    Liu, Yanzhou
    Crawford, James J.
    Braun, Marie-Gabrielle
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (18): : 8617 - 8624
12345