Regioselective C3-H Alkylation of Imidazopyridines with Donor-Acceptor Cyclopropanes

被引:6
|
作者
Dalkilic, Oguzhan [1 ]
Turbedaroglu, Ozge [1 ]
Lafzi, Ferruh [1 ]
Kilic, Haydar [1 ]
机构
[1] Ataturk Univ, Fac Sci, Dept Chem, TR-25240 Erzurum, Turkiye
来源
JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 16期
关键词
ACID; IMIDAZOHETEROCYCLES; DERIVATIVES; REACTIVITY; PROTOCOL; ION;
D O I
10.1021/acs.joc.3c01122
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Alkylated imidazopyridines are crucial structures formedicinalchemistry. Here, an efficient method for the C3-H alkylationof imidazopyridines was devised. Under Lewis acid-catalyzed conditions,reactions of imidazopyridines with different donor-acceptorcyclopropanes were carried out. Finally, 1,3-bisfunctionalizaton ofdonor-acceptor cyclopropanes was performed. In addition, synthesizedC3-alkylated imidazopyridines are amenable for diverse synthetic applications.
引用
收藏
页码:11834 / 11846
页数:13
相关论文
共 50 条
  • [21] Indole-derived Donor-acceptor Cyclopropanes
    Trushkov, Igor V.
    ISRAEL JOURNAL OF CHEMISTRY, 2016, 56 (6-7) : 369 - 384
  • [22] Donor-Acceptor Cyclopropanes: Activation Enabled by a Single, Vinylogous Acceptor
    Ahlburg, Nils L.
    Hergert, Oliver
    Jones, Peter G.
    Werz, Daniel B.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (01)
  • [23] Lewis acid-catalyzed regiodivergent N-alkylation of indazoles with donor-acceptor cyclopropanes
    Zhang, Xiaoyan
    Xiang, Yujiao
    Zhao, Xiangyang
    Zhou, Xin
    Chen, Weiliang
    Peng, Yungui
    ORGANIC CHEMISTRY FRONTIERS, 2025, 12 (03): : 766 - 771
  • [24] Diastereoselective (8+3)-Cycloadditions of Donor-Acceptor Cyclopropanes with Tropothione
    Mloston, Grzegorz
    Kowalczyk, Mateusz
    Palusiak, Marcin
    Oliver, Gwyndaf A.
    von Koeller, Heinrich F.
    Werz, Daniel B.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 27 (06)
  • [25] Asymmetric [3+n]-Cycloaddition Reactions of Donor-Acceptor Cyclopropanes
    Bao, Ming
    Doyle, Michael P.
    CHEMCATCHEM, 2023, 15 (23)
  • [26] [3+2] Annulation of Donor-Acceptor Cyclopropanes with Vinyl Azides
    Kaga, Atsushi
    Gandamana, Dhika Aditya
    Tamura, Sayako
    Demirelli, Mesut
    Chiba, Shunsuke
    SYNLETT, 2017, 28 (09) : 1091 - 1095
  • [27] Formal [3+2] cycloadditions of donor-acceptor cyclopropanes and nitriles
    Yu, M
    Pagenkopf, BL
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (27) : 8122 - 8123
  • [28] THE CARBENE COMPLEX ROUTE TO DONOR-ACCEPTOR SUBSTITUTED CYCLOPROPANES
    WIENAND, A
    BUCHERT, M
    HOFMANN, B
    REISSIG, HU
    ADVANCES IN METAL CARBENE CHEMISTRY, 1989, 269 : 271 - 273
  • [29] Uncovering the Neglected Similarities of Arynes and Donor-Acceptor Cyclopropanes
    Werz, Daniel B.
    Biju, Akkattu T.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (09) : 3385 - 3398
  • [30] Unprecedented reactivity of the donor-acceptor cyclopropanes in cycloadditions with nitrosoarene
    Vemula, Naresh
    Chidley, Tristan
    Pagenkopf, Brian
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2015, 250