Electrochemical thiocyanation of barbituric acids

Electrochemical thiocyanation of barbituric acids Full article

Journal

Organic and Biomolecular Chemistry
ISSN: 1477-0520 , E-ISSN: 1477-0539

Output data

Year: 2022, Volume: 20, Number: 17, Pages: 3629-3636 Pages count : 8 DOI: 10.1039/d2ob00343k

Authors

Bityukov Oleg V. ¹ , Kirillov Andrey S. ¹ , Serdyuchenko Pavel Yu. ^2,1 , Kuznetsova Maria A. ³ , Demidova Valentina N. ³ , Vil' Vera A. ¹ , Terent'ev Alexander O. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation
2	D. I. Mendeleev University of Chemical Technology of Russia, 9 Miusskaya Square, Moscow 125047, Russian Federation
3	All-Russian Research Institute for Phytopathology, B. Vyazyomy, 143050, Moscow Region, Russian Federation

The electrochemical thiocyanation of barbituric acids with NH4SCN was disclosed in an undivided cell under constant current conditions. The electrosynthesis is the most efficient at a record high current density (janode ≈50–70 mA cm−2). NH4SCN 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.

Bityukov O.V. , Kirillov A.S. , Serdyuchenko P.Y. , Kuznetsova M.A. , Demidova V.N. , Vil' V.A. , Terent'ev A.O.
Electrochemical thiocyanation of barbituric acids
Organic and Biomolecular Chemistry. 2022. V.20. N17. P.3629-3636. DOI: 10.1039/d2ob00343k WOS Scopus OpenAlex

Web of science:	WOS:000782936000001
Scopus:	2-s2.0-85129743285
OpenAlex:	W4223974324

DB	Citing
OpenAlex	12
Scopus	9
Web of science	11