Electrochemical thiocyanation of barbituric acids.

Autor: Bityukov OV; N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation. alterex@yandex.ru., Kirillov AS; N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation. alterex@yandex.ru., Serdyuchenko PY; N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation. alterex@yandex.ru.; D. I. Mendeleev University of Chemical Technology of Russia, 9 Miusskaya Square, Moscow 125047, Russian Federation., Kuznetsova MA; All-Russian Research Institute for Phytopathology, B. Vyazyomy, 143050, Moscow Region, Russian Federation., Demidova VN; All-Russian Research Institute for Phytopathology, B. Vyazyomy, 143050, Moscow Region, Russian Federation., Vil' VA; N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation. alterex@yandex.ru., Terent'ev AO; N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation. alterex@yandex.ru.
Jazyk: angličtina
Zdroj: Organic & biomolecular chemistry [Org Biomol Chem] 2022 May 04; Vol. 20 (17), pp. 3629-3636. Date of Electronic Publication: 2022 May 04.
DOI: 10.1039/d2ob00343k
Abstrakt: 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.
Databáze: MEDLINE
Externí odkaz: