Facile and clean electrochemical synthesis of new acetaminophen derivatives through electrochemical oxidation of acetaminophen in the presence of thiouracil derivatives
JOURNAL OF SULFUR CHEMISTRY, cilt.38, sa.2, ss.163-172, 2017 (SCI-Expanded, Scopus)
- Yayın Türü: Makale / Tam Makale
- Cilt numarası: 38 Sayı: 2
- Basım Tarihi: 2017
- Doi Numarası: 10.1080/17415993.2016.1262372
- Dergi Adı: JOURNAL OF SULFUR CHEMISTRY
- Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
- Sayfa Sayıları: ss.163-172
- Anahtar Kelimeler: Electrochemical oxidation, acetaminophen, thiouracil derivatives, cyclic voltammetry, Michael addition, GREEN MEDIA, MECHANISM
- Orta Doğu Teknik Üniversitesi Adresli: Hayır
Özet
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.