One-Pot N -α-C(sp3 )- H Bond Functionalisation Cascade for the Synthesis of Polysubstituted Imidazoles

被引：2
|
作者：
Kadu, Vikas D. [1 ]
Sankala, Naga Chandradudu [2 ]
Hublikar, Mahesh G. [1 ]
Bansode, Shahaji I. [1 ]
Bhosale, Raghunath B. [1 ]
机构：
[1] Punyashlok Ahilyadevi Holkar Solapur Univ, Sch Chem Sci, Solapur 413255, Maharashtra, India
[2] Rayalseema Univ, Dept Chem, Coll Engn, Kurnool 518002, Andhra Pradesh, India
来源：
SYNTHESIS-STUTTGART | 2024年 / 56卷 / 14期
关键词：
imidazoles; iron catalysis; oxidative coupling; N -alpha-C(sp(3) )- H functionalisation; one-pot reaction; TETRASUBSTITUTED IMIDAZOLES; PHOTOPHYSICAL PROPERTIES; SUBSTITUTED IMIDAZOLES; EFFICIENT SYNTHESIS; ANTIFUNGAL AGENTS; IRON CATALYSIS; METAL; AMINES; ANTIBACTERIAL; BENZYLAMINES;
D O I：
10.1055/s-0043-1763690
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A one-pot eco-friendly oxidative N-alpha-C(sp(3))-H bond functionalisation of arylmethylamines for the synthesis of tetrasubstituted imidazoles is demonstrated. The substrate scope of these amines has been well-explored with different substrates, such as 1,2-diketones, an alpha-hydroxy ketone and phenylacetophenone. In the presence of FeCl(3 )catalyst and green oxidant O-2, the easily accessible substrates afforded tetrasubstituted imidazoles in up to 94% yield.
引用
收藏
页码：2277 / 2283
页数：7
相关论文
共 50 条
  • [41] A convenient one-pot synthesis of polysubstituted pyrroles from N-protected succinimides
    Kobeissi, Marwan
    Yazbeck, Ogaritte
    Chreim, Yamama
    TETRAHEDRON LETTERS, 2014, 55 (15) : 2523 - 2526
  • [42] Photoexcited Pd(ii) auxiliaries enable light-induced control in C(sp3)-H bond functionalisation
    Czyz, Milena L.
    Weragoda, Geethika K.
    Horngren, Tyra H.
    Connell, Timothy U.
    Gomez, Daniel
    O'Hair, Richard A. J.
    Polyzos, Anastasios
    CHEMICAL SCIENCE, 2020, 11 (09) : 2455 - 2463
  • [43] Cascade C(sp3)-H bond functionalization/cyclization reaction for the synthesis of 3,3-disubstituted oxindoles by decatungstate photocatalysis
    Fang, Xianhe
    Lv, Jiaxing
    Yang, Shuxin
    Ma, Mingyu
    Yang, Runzhe
    Bi, Yi
    TETRAHEDRON, 2025, 177
  • [44] Intramolecular C(sp3)-H Bond Amination Strategies for the Synthesis of Saturated N-containing Heterocycles
    Zhang, Jiayu
    Perez-Temprano, Monica H.
    CHIMIA, 2020, 74 (11) : 895 - 903
  • [45] Palladium(ii)-catalyzed oxidative C(sp3)-P bond formation via C(sp3)-H bond activation
    Chen, Lijin
    Zhou, Zhenfei
    Zhang, Saifei
    Li, Xiaoqian
    Ma, Xuebing
    Dong, Jiaxing
    CHEMICAL COMMUNICATIONS, 2019, 55 (91) : 13693 - 13696
  • [46] Copper and zinc co-catalyzed synthesis of imidazoles via the activation of sp3 C-H and N-H bonds
    Tang, Dong
    Li, Xiao-Long
    Guo, Xin
    Wu, Ping
    Li, Ji-Hui
    Wang, Kai
    Jing, Huan-Wang
    Chen, Bao-Hua
    TETRAHEDRON, 2014, 70 (26) : 4038 - 4042
  • [47] Aqueous pulsed electrochemistry promotes C-N bond formation via a one-pot cascade approach
    He, Meng
    Wu, Yongmeng
    Li, Rui
    Wang, Yuting
    Liu, Cuibo
    Zhang, Bin
    NATURE COMMUNICATIONS, 2023, 14 (01)
  • [48] Electrochemical synthesis of α-amino amides via C(sp3)-H bond activation
    Guan, Zhipeng
    Peng, Yanan
    Yang, Dongfeng
    Zhu, Shuxiang
    Zhang, Heng
    Lei, Aiwen
    GREEN CHEMISTRY, 2022, 24 (10) : 3964 - 3968
  • [49] A Rh(III)-Catalyzed Cascade C-H Functionalization/C(sp3)-C(sp3) Formation/Cyclization Reaction for the Synthesis of Isoquinolinedione Derivatives
    Bai, Peng
    Huang, Kenneth L.
    Huang, Zhi-Zhen
    SYNTHESIS-STUTTGART, 2017, 49 (24): : 5357 - 5363
  • [50] Expeditious Synthesis of Spiroindoline Derivatives via Tandem C(sp2)-H and C(sp3)-H Bond Functionalization of N-Methyl-N-nitrosoanilines
    Wang, Kelin
    Sun, Yuqian
    Li, Bin
    Zhang, Xinying
    Fan, Xuesen
    ORGANIC LETTERS, 2024, 26 (15) : 3091 - 3096
12345