Electrochemical Oxidation of 3-Aryl-2-cyanothioacrylamides
V. I. Osminina, A. A. Mironenkoa, P. G. Dahnoa, M. A. Nazarenkoa, A. I. Oflidia, V. V. Dotsenkoa, b, *, V. D. Strelkova, b, N. A. Aksenovb, and I. V. Aksenovab
aKuban State University, Krasnodar, 350040 Russia
bNorth Caucasus Federal University, Stavropol, 355009 Russia
email: *victor_dotsenko_@mail.ru
Received 23 August, 2022
Abstract—
Electrochemical oxidation of (Е)-3-aryl-2-cyanoprop-2-enethioamides in a undivided cell in the presence of KBr in an aqueous or aqueous-organic medium has led to the formation of (2Е,2′E)-2,2′-(1,2,4-thiadiazole-3,5-diyl)bis[3-arylacrylonitriles] in 37–76% yield. A plausible reaction mechanism has been discussed. In laboratory experiments, (2E,2′E)-2,2′-(1,2,4-thiadiazol-3,5-diyl)bis[3-(4-methoxyphenyl)acrylonitrile] has revealed pronounced antidote effect against herbicide 2,4-D on sunflower seedlings and no pronounced growth-regulating properties.
Keywords:
thioamides,
oxidative dimerization,
electrochemical synthesis,
1,2,4-thiadiazoles,
growth-regulating activity,
antidote activity against 2,4-D
DOI: 10.1134/S1070363222110068