Electrochemical thiocyanation of barbituric acids

• Published in: Organic & biomolecular chemistry Vol. 2; no. 17; pp. 3629 - 3636
• Main Authors: Bityukov, Oleg V, Kirillov, Andrey S, Serdyuchenko, Pavel Yu, Kuznetsova, Maria A, Demidova, Valentina N, Vil', Vera A, Terent'ev, Alexander O
• Format: Journal Article
• Language: English
• Published: CAMBRIDGE Royal Soc Chemistry 04.05.2022; Royal Society of Chemistry
• Subjects: Acids; Antifungal activity; Barbiturates - chemistry; Barbiturates - pharmacology; Chemistry; Chemistry, Organic; Electrochemistry; Functional groups; Fungicides; Physical Sciences; Science & Technology; Tautomers; Thiocyanates; OXIDATION; AMMONIUM THIOCYANATE; TRIFLUOROMETHYLTHIOLATION; PARATHIOCYANOGEN; ALPHA-THIOCYANATION; OXIDANT; CATALYST; C-H FUNCTIONALIZATION; ANALGESICS; DERIVATIVES
• ISSN: 1477-0520; 1477-0539; 1477-0539
• DOI: 10.1039/d2ob00343k

The electrochemical thiocyanation of barbituric acids with NH 4 SCN was disclosed in an undivided cell under constant current conditions. The electrosynthesis is the most efficient at a record high current density ( j anode 50-70 mA cm −2 ). NH 4 SCN has a dual role as the source of the SCN group and as the electrolyte. Electrochemical thiocyanation of barbituric acids starts with the generation of (SCN) 2 from the thiocyanate anion. The addition of thiocyanogen to the double bond of the enol tautomer of barbituric acid gives thiocyanated barbituric acid. A variety of thiocyanated barbituric acids bearing different functional groups were obtained in 18-95% yields and were shown to exhibit promising antifungal activity. The electrochemical thiocyanation of barbituric acids with NH 4 SCN in an undivided cell at a record high current density was disclosed.