Electrochemical synthesis of 6-arylsulfonyl caffeic acid derivatives in aqueous medium

被引:32
|
作者
Zeng, Cheng-Chu [1 ]
Liu, Cheng-Fu [1 ]
Zeng, Jia [1 ]
Zhong, Ru-Gang [1 ]
机构
[1] Beijing Univ Technol, Coll Life Sci & Bioengn, Beijing 100022, Peoples R China
基金
中国国家自然科学基金;
关键词
caffeic acid; benzenesulfinate; organic electrochemical synthesis; cyclic voltammetry;
D O I
10.1016/j.jelechem.2007.02.005
中图分类号
O65 [分析化学];
学科分类号
070302 ; 081704 ;
摘要
The anodic oxidation of caffeic acid in the presence of sodium benzenesulfinate in aqueous solution was studied by cyclic voltammetry and controlled potential coulometry. The results showed that similar to other simple catechol derivatives where the substituents attached directly to the benzene ring, caffeic acid was oxidized to the corresponding o-benzoquinone which underwent further Michael-addition with sodium benzenesulfinate or sodium p-methyl benzenesulfinate to produce 6-arylsulfonyl caffeic acid derivative 7a or 7b. (c) 2007 Published by Elsevier B.V.
引用
收藏
页码:85 / 90
页数:6
相关论文
共 50 条
  • [21] A Concise Synthesis of Substituted Thiourea Derivatives in Aqueous Medium
    Maddani, Mahagundappa R.
    Prabhu, Kandikere R.
    JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (07): : 2327 - 2332
  • [22] Mechanism and thermodynamic study of electrochemical oxidation of Caffeic acid in the presence of Thiols: Electro-organic synthesis of new Caffeic acid thioethers
    Pakravan, Narges
    Beiginejad, Hadi
    Shayani-Jam, Hassan
    JOURNAL OF ELECTROANALYTICAL CHEMISTRY, 2020, 871
  • [23] Synthesis and electrochemical behaviour of β-halodehydroamino acid derivatives
    Paula M. T. Ferreira
    L. S. Monteiro
    G. Pereira
    Amino Acids, 2010, 39 : 499 - 513
  • [24] Synthesis and electrochemical behaviour of β-halodehydroamino acid derivatives
    Ferreira, Paula M. T.
    Monteiro, L. S.
    Pereira, G.
    AMINO ACIDS, 2010, 39 (02) : 499 - 513
  • [25] Synthesis of a series of caffeic acid phenethyl amide (CAPA) fluorinated derivatives: Comparison of cytoprotective effects to caffeic acid phenethyl ester (CAPE)
    Yang, John
    Marriner, Gwendolyn A.
    Wang, Xinyu
    Bowman, Phillip D.
    Kerwin, Sean M.
    Stavchansky, Salomon
    BIOORGANIC & MEDICINAL CHEMISTRY, 2010, 18 (14) : 5032 - 5038
  • [26] New Caffeic Acid Derivatives as Antimicrobial Agents: Design, Synthesis, Evaluation and Docking
    Merlani, Maia
    Barbakadze, Vakhtang
    Amiranashvili, Lela
    Gogilashvili, Lali
    Poroikov, Vladimir
    Petrou, Anthi
    Geronikaki, Athina
    Ciric, Aria
    Glamoclija, Jasmina
    Sokovic, Marina
    CURRENT TOPICS IN MEDICINAL CHEMISTRY, 2019, 19 (04) : 292 - 304
  • [27] One-Pot Electrochemical Synthesis of Fused Indole Derivatives Containing Active Hydroxyl Groups in Aqueous Medium
    Zeng, Cheng-Chu
    Liu, Fu-Jian
    Ping, Da-Wei
    Hu, Li-Ming
    Cai, Yuan-Li
    Zhong, Ru-Gang
    JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (16): : 6386 - 6389
  • [28] Improved production of caffeic acid derivatives in suspension cultures of Echinacea purpurea by medium replenishment strategy
    Wu, Chun-Hua
    Murthy, Hosalkatte Niranjana
    Hahn, Eun-Joo
    Paek, Kee-Yoeup
    ARCHIVES OF PHARMACAL RESEARCH, 2007, 30 (08) : 945 - 949
  • [29] Improved production of caffeic acid derivatives in suspension cultures ofEchinacea purpurea by medium replenishment strategy
    Chun-Hua Wu
    Hosakatte Niranjana Murthy
    Eun-Joo Hahn
    Kee-Yoeup Paek
    Archives of Pharmacal Research, 2007, 30 : 945 - 949
  • [30] Synthesis and Anti-oxidation Activity of Caffeic Acid Amino Acid Ethyl Ester Derivatives
    Wang, Dong
    Ma, Jin-Feng
    Cai, Ming-Xu
    Zhu, Jun
    Jingxi Huagong/Fine Chemicals, 2019, 36 (03): : 494 - 498