Metal-free approach for imidazole synthesis via one-pot N-α-C(sp3)-H bond functionalization of benzylamines

被引:2
|
作者
Kadu, Vikas D. [1 ]
Thokal, Machhindra S. [1 ]
Godase, Rajkumar K. [1 ]
Kotali, Bhagyashree C. [1 ]
Wadkar, Pooja S. [1 ]
机构
[1] Punyashlok Ahilyadevi Holkar Solapur Univ, Sch Chem Sci, Solapur 413255, Maharashtra, India
关键词
TETRASUBSTITUTED IMIDAZOLES; POLYSUBSTITUTED IMIDAZOLES; NITROGEN-HETEROCYCLES; EFFICIENT; ANTIBACTERIAL; CYCLIZATION; ANALOGS; DRUGS;
D O I
10.1039/d4ra03939d
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A metal-free one-pot method is established for the synthesis of tetrasubstituted imidazoles from the reaction of arylmethylamines and 1,2-dicarbonyls/benzoin. The N-alpha-C(sp(3))-H bond functionalization of arylmethylamines using a catalytic amount of AcOH afforded polysubstituted imidazoles under aerobic conditions in significant yields of up to 95%.
引用
收藏
页码:28332 / 28339
页数:8
相关论文
共 50 条
  • [1] Iodine-Mediated Domino Cyclization for One-Pot Synthesis of Indolizine-Fused Chromones via Metal-Free sp3 C-H Functionalization
    Zhang, Xiang-Jin
    Wang, Zhuo
    Zhang, Han
    Gao, Jing-Jing
    Yang, Kai-Rui
    Fan, Wei-Yu
    Wu, Rui-Xue
    Feng, Meng-Lin
    Zhu, Wei
    Zhu, Yan-Ping
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (01): : 835 - 845
  • [2] Practical, metal-free remote heteroarylation of amides via unactivated C(sp3)-H bond functionalization
    Tang, Nana
    Wu, Xinxin
    Zhu, Chen
    CHEMICAL SCIENCE, 2019, 10 (28) : 6915 - 6919
  • [3] α-Arylchalcogenation of acetone with diaryl dichalcogenide via metal-free oxidative C(sp3)-H bond functionalization
    Yan, Guobing
    Borah, Arun Jyoti
    Wang, Lianggui
    Pan, Zhangjin
    Chen, Shuangshuang
    Shen, Xuqian
    Wu, Xiangmei
    TETRAHEDRON LETTERS, 2015, 56 (29) : 4305 - 4307
  • [4] One-Pot N -α-C(sp3 )- H Bond Functionalisation Cascade for the Synthesis of Polysubstituted Imidazoles
    Kadu, Vikas D.
    Sankala, Naga Chandradudu
    Hublikar, Mahesh G.
    Bansode, Shahaji I.
    Bhosale, Raghunath B.
    SYNTHESIS-STUTTGART, 2024, 56 (14): : 2277 - 2283
  • [5] I2 promoted domino oxidative cyclization for one-pot synthesis of 2-acylbenzothiazoles via metal-free sp3 C-H functionalization
    Zhu, Yan-Ping
    Lian, Mi
    Jia, Feng-Cheng
    Liu, Mei-Cai
    Yuan, Jing-Jing
    Gao, Qing-He
    Wu, An-Xin
    CHEMICAL COMMUNICATIONS, 2012, 48 (72) : 9086 - 9088
  • [6] One-pot synthesis of benzoxazoles via the metal-free ortho-C-H functionalization of phenols with nitroalkanes
    Aksenov, Nicolai A.
    Aksenov, Alexander V.
    Nadein, Oleg N.
    Aksenov, Dmitrii A.
    Smirnov, Alexander N.
    Rubin, Michael
    RSC ADVANCES, 2015, 5 (88): : 71620 - 71626
  • [7] Rapid One-Pot Aerobic Oxidative N-α-C(sp3)-H Functionalization of Arylmethylamines to Access Tetrasubstituted Imidazoles
    Kadu, Vikas D.
    Khadul, Siddheshwar P.
    Kothe, Gokul J.
    Mali, Ganesh A.
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 11 (08)
  • [8] Recent Development of Metal-Free Direct Asymmetric Functionalization of Benzylic C(sp3)-H Bond
    Jiang, Xin
    Wang, Sidun
    Guo, Guimin
    Lu, Beili
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2017, 37 (04) : 841 - 857
  • [9] Metal-Free Oxidative C(sp3)-H Bond Functionalization of Alkanes and Conjugate Addition to Chromones
    Zhao, Jincan
    Fang, Hong
    Qian, Ping
    Han, Jianlin
    Pan, Yi
    ORGANIC LETTERS, 2014, 16 (20) : 5342 - 5345
  • [10] Metal-free oxidative functionalization of C(sp3)-H of ketones and alcohols for the synthesis of isoquinolinonediones
    Zhu, Su-Li
    Zhou, Ping-Xin
    Xia, Xiao-Feng
    RSC ADVANCES, 2016, 6 (68): : 63325 - 63330