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
  • [21] n-Bu4NI-catalyzed selective dual amination of sp3 C-H bonds: oxidative domino synthesis of imidazo[1,5-c]quinazolines on a gram-scale
    Zhao, Dan
    Wang, Teng
    Shen, Qi
    Li, Jian-Xin
    CHEMICAL COMMUNICATIONS, 2014, 50 (33) : 4302 - 4304
  • [22] Iodine-Mediated δ-Amination of sp3 C-H Bonds
    Ye, Wenjun
    Xiong, Hanyu
    Wang, Manman
    Chang, Junbiao
    Yu, Wenquan
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (05): : 3481 - 3490
  • [23] Synthesis of imidazo[1,5-a]pyridines via oxidative amination of the C(sp3)-H bond under air using metal-organic framework Cu-MOF-74 as an efficient heterogeneous catalyst
    Nguyen, Hanh T. H.
    Nguyen, Oanh T. K.
    Thanh Truong
    Phan, Nam T. S.
    RSC ADVANCES, 2016, 6 (42) : 36039 - 36049
  • [24] Flavin-Iodine-Catalyzed Aerobic Oxidative Tandem C(sp3)-H Imination and Amination: Synthesis of Fluorescent Imidazo[1,5-a]pyridines from Pyridylmethanes and Aminomethanes
    Fukuda, Tatsuki
    Miyake, Hazuki
    Abe, Sota
    Yagishita, Fumitoshi
    Iida, Hiroki
    ADVANCED SYNTHESIS & CATALYSIS, 2025, 367 (02)
  • [25] Electrochemical oxidative synthesis of 2-benzoylquinazolin-4(3H)-one via C(sp3)-H amination under metal-free conditions
    Hu, Yongzhi
    Ma, Xinhua
    Hou, Huiqing
    Sun, Weiming
    Tu, Shuqing
    Wu, Mei
    Lin, Rongkun
    Xu, Xiuzhi
    Ke, Fang
    CATALYSIS SCIENCE & TECHNOLOGY, 2021, 11 (19) : 6374 - 6379
  • [26] Cleavage of sp3 C-O Bonds via Oxidative Addition of C-H Bonds
    Choi, Jongwook
    Choliy, Yuriy
    Zhang, Xiawei
    Emge, Thomas J.
    Krogh-Jespersen, Karsten
    Goldman, Alan S.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (43) : 15627 - +
  • [27] Metal-free oxidative functionalization of C(sp3)-H of ketones and alcohols for the synthesis of isoquinolinonediones
    Zhu, Su-Li
    Zhou, Ping-Xin
    Xia, Xiao-Feng
    RSC ADVANCES, 2016, 6 (68): : 63325 - 63330
  • [28] Metal-Free One-Pot Three-Component Synthesis of Quinazoline Derivatives via Peroxide-Mediated Direct Oxidative Amination of C(sp3)-H Bonds
    Huynh, Tien, V
    Doan, Son H.
    Trinh, Khang H.
    Ly, Trang H.
    Phan, Anh L. T.
    Nguyen, Tung T.
    Phan, Anh N. Q.
    Phan, Nam T. S.
    CHEMISTRYSELECT, 2019, 4 (40): : 11808 - 11814
  • [29] Metal-free oxidative hydroxyalkylarylation of activated alkenes by direct sp3 C-H functionalization of alcohols
    Meng, Yuan
    Guo, Li-Na
    Wang, Hua
    Duan, Xin-Hua
    CHEMICAL COMMUNICATIONS, 2013, 49 (68) : 7540 - 7542
  • [30] Metal-free DDQ-mediated oxidative C-O coupling of acetalic sp3 C-H bonds with carboxylic acids
    Li, Jiang-Sheng
    Xue, Yuan
    Fu, Dong-Mei
    Li, Dao-Lin
    Li, Zhi-Wei
    Liu, Wei-Dong
    Pang, Huai-Lin
    Zhang, Yue-Fei
    Cao, Zhong
    Zhang, Ling
    RSC ADVANCES, 2014, 4 (96) : 54039 - 54042