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
  • [31] Metal-Free Oxidative C-H Bond Amination at Ambient Temperature
    Samanta, Rajarshi
    Antonchick, Andrey P.
    SYNLETT, 2012, (06) : 809 - 813
  • [32] Metal-free amidation of ether sp3 C-H bonds with sulfonamides using PhI(OAc)2
    Campos, Jesus
    Goforth, Sarah K.
    Crabtree, Robert H.
    Gunnoe, T. Brent
    RSC ADVANCES, 2014, 4 (89) : 47951 - 47957
  • [33] Metal-free oxidative cross-dehydrogenative coupling of quinones with benzylic C(sp3)-H bonds
    Dong, Yu
    Yang, Jian
    He, Shuai
    Shi, Zhi-Chuan
    Wang, Yu
    Zhang, Xiao-Mei
    Wang, Ji-Yu
    RSC ADVANCES, 2019, 9 (47) : 27588 - 27592
  • [34] Synthesis of Lactones via C-H Functionalization of Nonactivated C(sp3)-H Bonds
    Richers, Johannes
    Heilmann, Michael
    Drees, Markus
    Tiefenbacher, Konrad
    ORGANIC LETTERS, 2016, 18 (24) : 6472 - 6475
  • [35] Visible light mediated synthesis of 1,3-diarylated imidazo[1,5-a]pyridines via oxidative amination of C-H catalyzed by graphitic carbon nitride
    Talpada, Nandish
    Sharma, Anuj S.
    Sharma, Vinay S.
    Varma, Rajender S.
    Shrivastav, Pranav S.
    Ahmed, Rahul
    Sudhakar, Achalkumar Ammathnadu
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (48) : 9552 - 9561
  • [36] Metal-Free Allylic C-H Amination
    Murakami S.
    Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry, 2023, 81 (03): : 267 - 268
  • [37] Metal-Free Allylic C-H Amination
    Murakami, Suguru
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2023, 81 (03) : 267 - 268
  • [38] Metal-free, highly efficient organocatalytic amination of benzylic C-H bonds
    Xue, Qicai
    Xie, Jin
    Li, Huamin
    Cheng, Yixiang
    Zhu, Chengjian
    CHEMICAL COMMUNICATIONS, 2013, 49 (35) : 3700 - 3702
  • [39] Metal-free synthesis of indolizines through oxidative C-C and C-N bond formations of C (sp3)-H bonds
    Reddy, N. Naresh Kumar
    Mohan, Darapaneni Chandra
    Adimurthy, Subbarayappa
    TETRAHEDRON LETTERS, 2016, 57 (10) : 1074 - 1078
  • [40] Primary amination of C(sp3)-H bonds
    Voller, Jan-Stefan
    NATURE CATALYSIS, 2020, 3 (06) : 473 - 473