Facile and clean electrochemical synthesis of new acetaminophen derivatives through electrochemical oxidation of acetaminophen in the presence of thiouracil derivatives


Asghari A., Ameri M. , Taghipour S., Ghaderi O.

JOURNAL OF SULFUR CHEMISTRY, vol.38, no.2, pp.163-172, 2017 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 38 Issue: 2
  • Publication Date: 2017
  • Doi Number: 10.1080/17415993.2016.1262372
  • Title of Journal : JOURNAL OF SULFUR CHEMISTRY
  • Page Numbers: pp.163-172
  • Keywords: Electrochemical oxidation, acetaminophen, thiouracil derivatives, cyclic voltammetry, Michael addition, GREEN MEDIA, MECHANISM

Abstract

The electrochemical oxidation of acetaminophen (1a) is carried out in the presence of thiouracil derivatives (3a-c), as nucleophiles, in an acetate buffer solution (0.15M, pH 5) mixed with Dimethylformamide (DMF) using cyclic voltammetry and coulometry under a constant potential. The results obtained indicate that N-acetyl-p-benzoquinone-imine derived from acetaminophen participates in a 1,4-Michael-type addition reaction with thiouracils to form the corresponding acetaminophen derivatives (4a-c) in good yields and with high purities using a facile, catalyst-free, and one-pot electrochemical method using three carbon electrodes in an undivided cell under mild conditions. The products obtained were characterized after purification by IR, H-1 NMR, and C-13 NMR spectroscopies, and by the elemental analysis method.