4.4 Article

Electrochemical oxidation of catechols in the presence of 4-mercapto-benzoic acid, to synthesis sulfanyl compounds and their biological studies

Journal

TETRAHEDRON
Volume 71, Issue 11, Pages 1674-1678

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2015.01.057

Keywords

Catechol; 4-Mercapto-bezoic acid; Electrochemical oxidation; Michael reaction; Antimicrobial activity

Funding

  1. Chinese Scholarship Council (CSC) [2012GXZ174]
  2. National Natural Science Foundation of China [51374016]

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Electrochemical oxidation of catechols in the presence of 4-mercapto-benzoic acid as nucleophile have been studied in aqueous acetate buffer solution using cyclic voltammetry and control potential coulometry. The cyclic voltammetric results showed that an electro oxidative/Michael type sequential reaction occurs between the 4-mercaptide anion and electrochemically generated o-bezoquinones leading to the corresponding products 4a-4b. The mechanism electrochemical reaction is proved as an EC pathway using controlled-potential coulometry. The antimicrobial activity of these newly synthesized compounds were screened against Gram-positive and Gram-negative bacteria namely, Bacillus subtilis, Staphylococcus aureus, Escherichia coli. These newly syntheses compounds showed good antimicrobial activity. (C) 2015 Elsevier Ltd. All rights reserved.

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