Oxidation of 2-Cyanothioacrylamides with Sodium Nitrite in Acidic Medium
P. G. Dahnoa, D. M. Zhilyaeva, V. V. Dotsenkoa, b, *, V. D. Strelkova, G. D. Krapivinc, N. A. Aksenovb, I. V. Aksenovab, and N. G. Likhovidb
aKuban State University, Krasnodar, 350040 Russia
bNorth Caucasus Federal University, Stavropol, 355009 Russia
cKuban State Technological University, Krasnodar, 350072 Russia
email: *victor_dotsenko_@mail.ru
Received 23 July, 2022
Abstract—
(E)-3-Aryl-2-cyanoprop-2-entioamides, prepared by Knoevenagel condensation between aromatic aldehydes and cyanothioacetamide, react with sodium nitrite in acetic acid to form (2E,2′E)-2,2′-(1,2,4-thiadiazole-3,5-diyl)bis[3-arylacrylonitriles]. A possible mechanism and limitations of the reaction are discussed. Molecular docking was carried out in order to search for possible protein targets for the obtained 1,2,4-thiadiazoles. One of the compounds showed a pronounced antidote effect against the herbicide 2,4-D in a laboratory experiment on sunflower seedlings and under field conditions.
Keywords:
cyanothioacetamide,
thioamides,
2-cyanothioacrylamides,
oxidative dimerization,
1,2,4-thiadiazoles
DOI: 10.1134/S1070363222090080