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Title: Mannich Reaction Involving 6-Amino-4-methyl-2-(thio)oxo-1,2-dihydropyridine-3,5-dicarbonitriles
Authors: Strelkov, V. D.
Стрелков, В. Д.
Dotsenko, V. V.
Доценко, В. В.
Aksenov, N. A.
Аксенов, Н. А.
Aksenova, I. V.
Аксенова, И. В.
Keywords: 2,4-D antidotes;Pyrido[1,2-a][1,3,5]triazines;2-aminopyridines;2-oxopyridines;Aminomethylation;Mannich reaction;Corrosion inhibitors;Nicotinonitriles
Issue Date: 2023
Citation: Panaetov, A.O., Strelkov, V.D., Dotsenko, V.V., Aksenov, N.A., Aksenova, I.V., Chausov, F.F., Lomova, N.V., Kazantseva, I.S., Isupov, N.Y. Mannich Reaction Involving 6-Amino-4-methyl-2-(thio)oxo-1,2-dihydropyridine-3,5-dicarbonitriles // Russian Journal of General Chemistry. - 2023. - 93 (7), pp. 1655-1668. - DOI: 10.1134/S1070363223070046
Series/Report no.: Russian Journal of General Chemistry
Abstract: The reaction of (1-ethoxyethylidene)malononitrile with cyanoacetamide or cyanothioacetamide has yielded 6-amino-4-methyl-2-(thio)oxo-1,2-dihydropyridine-3,5-dicarbonitriles. The resulting pyridine derivatives enter into the aminomethylation reaction with an excess of formaldehyde and primary amines with the formation of previously unknown 8-methyl-6-oxo-3-R-1,3,4,6-tetrahydro-2H-pyrido[1,2-a][1,3,5]triazine-7,9-dicarbonitriles. Further treatment of 6-amino-4-methyl-2-thioxo-1,2-dihydropyridine-3,5-dicarbonitrile and its oxygen analog with excess of formaldehyde has led to the formation of 3,10-dimethyl-1,8-dithioxo-5,6,12,13-tetrahydro-1H,8H-dipyrido[1,2-a:1′,2′-e][1,3,5,7]tetrazocin-2,4,9,11-tetracarbonitrile and 6,6′-[methylenedi(imino)]bis(4-methyl-2-oxo-1,2-dihydropyridine-3,5-dicarbonitrile), respectively. These compounds have shown a pronounced antidote effect against the herbicide 2,4-D (2,4-dichlorophenoxyacetic acid) in laboratory and field experiments on sunflower seedlings. Furthermore, 6-amino-4-methyl-2-oxo-1,2-dihydropyridine-3,5-dicarbonitrile has exhibited pronounced anticorrosion properties, acting as an adsorption-type corrosion inhibitor. The mechanism of the anticorrosion action has been investigated in detail using X-ray photoelectron spectroscopy.
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