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

Date

2017-04-01

Author

Asghari, Alireza
Ameri, Mohsen
Taghipour, Samira
Ghaderi, Omid

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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.

URI

https://hdl.handle.net/11511/94356

Journal

JOURNAL OF SULFUR CHEMISTRY

DOI

https://doi.org/10.1080/17415993.2016.1262372

Collections

Center for Solar Energy Research and Applications (GÜNAM), Article

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Citation Formats

A. Asghari, M. Ameri, S. Taghipour, and O. Ghaderi, “Facile and clean electrochemical synthesis of new acetaminophen derivatives through electrochemical oxidation of acetaminophen in the presence of thiouracil derivatives,” JOURNAL OF SULFUR CHEMISTRY, vol. 38, no. 2, pp. 163–172, 2017, Accessed: 00, 2021. [Online]. Available: https://hdl.handle.net/11511/94356.