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
  • [31] Recent advances in the diastereoconvergent synthesis of donor-acceptor cyclopropanes
    Prosser, Anthony R.
    Rubin, Michael
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 241
  • [32] Oligopyrrole synthesis by domino reactions of donor-acceptor cyclopropanes
    Werz, Daniel B.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 248
  • [33] HFIP & Bronsted Acid Promoted Direct Distal C-Alkylation of 2-Oxindoles and Anilines with Donor-Acceptor Cyclopropanes
    Singh, Prasoon Raj
    Lamba, Manisha
    Singh, Divyasha
    Goswami, Avijit
    ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (10) : 1685 - 1692
  • [34] ALKYLATION OF DONOR-ACCEPTOR SUBSTITUTED CYCLOPROPANES - A FLEXIBLE ROUTE TO 4-OXOCARBOXYLIC ACID-ESTERS
    BOHM, I
    HIRSCH, E
    REISSIG, HU
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1981, 20 (6-7): : 574 - 574
  • [35] Mechanochemistry Enabled Friedel-Crafts Alkylation Reactions of Donor-Acceptor Cyclopropanes with 2-Indolymethanols
    Liang, Jinshao
    Ruan, Lihong
    Shi, Xurong
    Chen, Yinzhi
    Song, Chuhuang
    Xiao, Jun'an
    Liu, Zhiping
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2024, 44 (11) : 3437 - 3445
  • [36] Donor-acceptor cyclopropanes as building blocks in (3+2) annulation reactions
    Parsons, Andrew T.
    Smith, Austin G.
    Johnson, Jeffrey S.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2010, 240
  • [37] Carbanion-Induced [3+2] Annulation of Donor-Acceptor Cyclopropanes
    Sasaki, Michiko
    Kondo, Yasuhiro
    Nishio, Takuya
    Takeda, Kei
    ORGANIC LETTERS, 2016, 18 (15) : 3858 - 3861
  • [38] Tetrahydroquinolines via Stereospecific [3+3]-Annulation of Donor-Acceptor Cyclopropanes with Nitrosoarenes
    Das, Saikat
    Chakrabarty, Shyamal
    Daniliuc, Constantin G.
    Studer, Armido
    ORGANIC LETTERS, 2016, 18 (11) : 2784 - 2787
  • [39] GaCl3-Mediated Reactions of Donor-Acceptor Cyclopropanes with Aromatic Aldehydes
    Borisov, Denis D.
    Novikov, Roman A.
    Tomilov, Yury V.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (40) : 12233 - 12237
  • [40] Visible-light-mediated regioselective ring-opening hydrogenolysis of donor-acceptor cyclopropanes with DIPEA and H2O
    Liu, Zhen
    Wei, Yin
    Shi, Min
    ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (07): : 1960 - 1966
12345