Urazoles as Heterocyclic Directing Groups in Ru(II)-Catalyzed Annulation of N-H/C-H Bonds with Vinylene Carbonate

被引:1
|
作者
Kang, Jungmin [1 ]
Park, Jihye [1 ]
Singh, Pargat [1 ]
Jeong, Taejoo [1 ]
Kim, In Su [1 ]
机构
[1] Sungkyunkwan Univ, Sch Pharm, Suwon 16419, South Korea
基金
新加坡国家研究基金会;
关键词
BIOCONJUGATION; ACTIVATION; INHIBITORS; TYROSINE;
D O I
10.1021/acs.joc.4c02033
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The development of novel directing groups is a valuable strategy to secure the advancement of catalytic C-H functionalization. To illustrate the feasibility of urazoles as heterocyclic directing groups, we herein present the ruthenium(II)-catalyzed annulation of N-H/C-H bonds on N-aryl urazoles with vinylene carbonate. This transformation provides the rapid construction of triazolocinnoline derivatives as hemiaminal and dehydrated forms. A series of mechanistic investigations and post-transformations highlighted the amenability of the developed method.
引用
收藏
页数:11
相关论文
共 50 条
  • [21] CoIII-Catalyzed Isonitrile Insertion/Acyl Group Migration Between C-H and N-H bonds of Arylamides
    Kalsi, Deepti
    Barsu, Nagaraju
    Sundararaju, Basker
    CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (10) : 2360 - 2364
  • [22] Ni(H)-Catalyzed Sulfonylation of ortho C-H Bonds in Aromatic Amides Utilizing an N,N-Bidentate Directing Group
    Yokota, Ayana
    Chatani, Naoto
    CHEMISTRY LETTERS, 2015, 44 (07) : 902 - 904
  • [23] Ni(II) catalyzed bromination of aryl C-H bonds
    Bhattacharya, Moumita
    Cluff, David B.
    Das, Siddhartha
    INORGANICA CHIMICA ACTA, 2014, 423 : 238 - 241
  • [24] Synthesis of Vinyl-Substituted Dihydroisoquinolone via Ru(II)-Catalyzed C-H Functionalization/Annulation of Imidates
    Lin, Cong
    Gao, Zhenbo
    Teng, Qiuxun
    Xue, Bowen
    Li, Xiaohua
    Gao, Fei
    Shen, Liang
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2020, 40 (09) : 2863 - 2870
  • [25] Oxidative C-H/N-H Annulation of Aromatic Amides with Dialkyl Malonates: Access to Isoindolinones and Dihydrobenzoindoles
    Pradhan, Sourav
    Roy, Subhasish
    Banerjee, Sonbidya
    De, Pinaki Bhusan
    Punniyamurthy, Tharmalingam
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (08) : 5741 - 5749
  • [26] Palladium-Catalyzed Olefination of Aryl C-H Bonds by Using Directing Scaffolds
    Bag, Sukdev
    Maiti, Debabrata
    SYNTHESIS-STUTTGART, 2016, 48 (06): : 804 - 815
  • [27] Isoindolinone synthesis through Rh/Cu-catalyzed oxidative C-H/N-H annulation of N-methoxy benzamides with saturated ketones
    Du, Xiao
    Hu, Yuntao
    Yang, Darun
    Huang, Decai
    Yang, Wendi
    Wu, Hailong
    Zhao, Huaiqing
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (04) : 783 - 789
  • [28] The Nickel/Copper-Catalyzed Direct Alkylation of Heterocyclic C-H Bonds
    Vechorkin, Oleg
    Proust, Valerie
    Hu, Xile
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (17) : 3061 - 3064
  • [29] Activation reactions of ru-catalyzed arylic or olefinic C-H bonds
    Yu, SC
    Ma, SM
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2002, 22 (05) : 307 - 317
  • [30] Synthesis of pyrazolo[5,1-a]isoquinolines via C-H/N-H annulation of pyrazoles and alkynes with ruthenium(II) catalysts
    Singh, Keisham Sarjit
    Goankar, Ramila R.
    Banerjee, Kushal
    Kaminsky, Werner
    MONATSHEFTE FUR CHEMIE, 2023, 154 (08): : 905 - 914