Copper-catalyzed Synthesis of Amides from Alcohols and Aminopyridines Under Aerobic Conditions

被引：0
|
作者：
Yang, Wei [1 ,2 ]
Liu, Jiaqi [1 ]
Tang, Cuiman [1 ]
Zhang, Haonan [1 ]
Wang, Bingbing [1 ]
Sun, Zhong [1 ]
Xu, Xiaohui [1 ]
机构：
[1] Northeast Elect Power Univ, Sch Chem Engn, Jilin 132012, Jilin, Peoples R China
[2] Gongqing Inst Sci & Technol, Jiujiang 332020, Peoples R China
来源：
CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE | 2023年 / 44卷 / 08期
关键词：
Copper-catalyzed synthesis; Aerobic; Alcohol; Amide; DIRECT OXIDATIVE AMIDATION; BENZYL ALCOHOLS; ROOM-TEMPERATURE; BOND FORMATION; ALDEHYDES; AMINES; NANOPARTICLES; HYDRATION;
D O I：
10.7503/cjcu20230029
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
N-(pyridine-2-yl)amides were synthesized in one step with benzyl alcohols and 2-aminopyridines in copper-catalyzed aerobic conditions by air bubbling method. The mechanism study demonstrated that benzaldehydes were formed in situ from benzyl alcohols under aerobic conditions and acted as coupling partners to react with 2-aminopyridines to synthesize amides. The bioactivity study showed that the synthesized products possessed certain antibacterial activity. This reaction features high efficiency and functional group tolerance. Moreover, no additives were used in the reaction and this method utilized oxygen from the air as an ideal oxidant with the virtue of economy and green.
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页数：6
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共 34 条
  • [1] Catalytic Acylation of Amines with Aldehydes or Aldoximes
    Allen, C. Liana
    Davulcu, Simge
    Williams, Jonathan M. J.
    [J]. ORGANIC LETTERS, 2010, 12 (22) : 5096 - 5099
  • [2] Direct oxidative amidation of benzyl alcohols using EDTA@Cu(II) functionalized superparamagnetic nanoparticles
    Azizi, Kobra
    Karimi, Meghdad
    Nikbakht, Fatemeh
    Heydari, Akbar
    [J]. APPLIED CATALYSIS A-GENERAL, 2014, 482 : 336 - 343
  • [3] Iron/Caffeine as a Catalytic System for Microwave-Promoted Benzamide Formation
    Bantreil, Xavier
    Navals, Pauline
    Martinez, Jean
    Lamaty, Frederic
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (02) : 417 - 422
  • [4] Iron-catalyzed benzamide formation. Application to the synthesis of moclobemide
    Bantreil, Xavier
    Kanfar, Nasreddine
    Gehin, Nicolas
    Golliard, Ethan
    Ohlmann, Pauline
    Martinez, Jean
    Lamaty, Frederic
    [J]. TETRAHEDRON, 2014, 70 (34) : 5093 - 5099
  • [5] General approach to the coupling of organoindium reagents with imines via copper catalysis
    Black, DA
    Arndtsen, BA
    [J]. ORGANIC LETTERS, 2006, 8 (10) : 1991 - 1993
  • [6] Ce(III)-catalyzed highly efficient synthesis of pyridyl benzamides from aminopyridines and nitroolefins without external oxidants
    Chen, Zhengwang
    Wen, Xiaowei
    Qian, Yiping
    Liang, Pei
    Liu, Botao
    Ye, Min
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (08) : 1247 - 1251
  • [7] Co2(CO)8 as a Solid CO (g) Source for the Amino Carbonylation of (Hetero)aryl Halides with Highly Deactivated (Hetero)arylamines
    Cheruku, Srinivas
    Sajith, Ayyiliath M.
    Narayana, Yatheesh
    Shetty, Poornima
    Nagarakere, Sandhya C.
    Sagar, Kunigal S.
    Manikyanally, Kumara N.
    Rangappa, Kanchugarkoppal Subbegowda
    Mantelingu, Kempegowda
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (08): : 5530 - 5537
  • [8] Copper-catalyzed hydrative amide synthesis with terminal alkyne, sulfonyl azide, and water
    Cho, SH
    Yoo, EJ
    Bae, L
    Chang, S
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (46) : 16046 - 16047
  • [9] Transformation of aldehydes or alcohols to amides at room temperature under aqueous conditions
    Dong, Dao-Qing
    Hao, Shuang-Hong
    Zhang, Hui
    Wang, Zu-Li
    [J]. CHINESE CHEMICAL LETTERS, 2017, 28 (07) : 1597 - 1599
  • [10] Direct oxidative amidation of aldehydes with anilines under mechanical milling conditions
    Gao, Jie
    Wang, Guan-Wu
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (07): : 2955 - 2958
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