Showing papers in "Russian Journal of General Chemistry in 2022"

Oxidation of 2-Cyanothioacrylamides with Sodium Nitrite in Acidic Medium

Abstract: 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 (2 E ,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.

Synthesis and Aminomethylation of 2-Amino-4-(2-chlorophenyl)-6-(dicyanomethyl)-1,4-dihydropyridine-3,5-dicarbonitrile N-Methylmorpholinium Salt

Abstract: Sequential reaction of 2-chlorobenzaldehyde, cyanothioacetamide, and malononitrile dimer in the presence of an excess of N-methylmorpholine resulted in the formation of N-methylmorphlinium salt of 2-amino-4-(2-chlorophenyl)-6-(dicyanomethyl)-1,4-dihydropyridine-3,5-dicarbonitrile. The resulting salt reacts under Mannich conditions with primary amines and an excess of formaldehyde to form substituted 2-alkylamino-4-(dicyanomethylene)-3,7-diazabicyclo[3.3.1]non-2-ene-1,5-dicarbonitriles. Structure of the key compound was confirmed by single crystal X-ray diffraction analysis.