Electrochemical thiocyanation of barbituric acids

被引：11

作者：

Bityukov, Oleg, V ^{[1
]}

Kirillov, Andrey S. ^{[1
]}

Serdyuchenko, Pavel Yu ^{[1
,2
]}

Kuznetsova, Maria A. ^{[3
]}

Demidova, Valentina N. ^{[3
]}

Vil, Vera A. ^{[1
]}

Terent'ev, Alexander O. ^{[1
]}

机构：

[1] Russian Acad Sci, ND Zelinsky Inst Organ Chem, 47 Leninsky Prosp, Moscow 119991, Russia

[2] DI Mendeleev Univ Chem Technol Russia, 9 Miusskaya Sq, Moscow 125047, Russia

[3] All Russian Res Inst Phytopathol, B Vyazyomy 143050, Moscow Region, Russia

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2022年 / 20卷 / 17期

基金：

俄罗斯科学基金会;

关键词：

C-H FUNCTIONALIZATION; AMMONIUM THIOCYANATE; ALPHA-THIOCYANATION; DERIVATIVES; OXIDATION; CATALYST; OXIDANT; TRIFLUOROMETHYLTHIOLATION; PARATHIOCYANOGEN; ANALGESICS;

D O I：

10.1039/d2ob00343k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 (j(anode) approximate to 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.

引用

页码：3629 / 3636

页数：8

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