Mannich Reaction Involving 6-Amino-4-methyl-2-(thio)oxo-1,2-dihydropyridine-3,5-dicarbonitriles

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...

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Bibliografische gegevens
Hoofdauteurs:	Strelkov, V. D., Стрелков, В. Д., Dotsenko, V. V., Доценко, В. В., Aksenov, N. A., Аксенов, Н. А., Aksenova, I. V., Аксенова, И. В.
Formaat:	Статья
Taal:	English
Gepubliceerd in:	2023
Onderwerpen:	2,4-D antidotes Pyrido[1,2-a][1,3,5]triazines 2-aminopyridines 2-oxopyridines Aminomethylation Mannich reaction Corrosion inhibitors Nicotinonitriles
Online toegang:	https://dspace.ncfu.ru/handle/20.500.12258/25524
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spelling	ir-20.500.12258-255242023-09-20T14:09:11Z Mannich Reaction Involving 6-Amino-4-methyl-2-(thio)oxo-1,2-dihydropyridine-3,5-dicarbonitriles Strelkov, V. D. Стрелков, В. Д. Dotsenko, V. V. Доценко, В. В. Aksenov, N. A. Аксенов, Н. А. Aksenova, I. V. Аксенова, И. В. 2,4-D antidotes Pyrido[1,2-a][1,3,5]triazines 2-aminopyridines 2-oxopyridines Aminomethylation Mannich reaction Corrosion inhibitors Nicotinonitriles 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. 2023-09-20T14:08:04Z 2023-09-20T14:08:04Z 2023 Статья 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 http://hdl.handle.net/20.500.12258/25524 en Russian Journal of General Chemistry application/pdf application/pdf
institution	СКФУ
collection	Репозиторий
language	English
topic	2,4-D antidotes Pyrido[1,2-a][1,3,5]triazines 2-aminopyridines 2-oxopyridines Aminomethylation Mannich reaction Corrosion inhibitors Nicotinonitriles
spellingShingle	2,4-D antidotes Pyrido[1,2-a][1,3,5]triazines 2-aminopyridines 2-oxopyridines Aminomethylation Mannich reaction Corrosion inhibitors Nicotinonitriles Strelkov, V. D. Стрелков, В. Д. Dotsenko, V. V. Доценко, В. В. Aksenov, N. A. Аксенов, Н. А. Aksenova, I. V. Аксенова, И. В. Mannich Reaction Involving 6-Amino-4-methyl-2-(thio)oxo-1,2-dihydropyridine-3,5-dicarbonitriles
description	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.
format	Статья
author	Strelkov, V. D. Стрелков, В. Д. Dotsenko, V. V. Доценко, В. В. Aksenov, N. A. Аксенов, Н. А. Aksenova, I. V. Аксенова, И. В.
author_facet	Strelkov, V. D. Стрелков, В. Д. Dotsenko, V. V. Доценко, В. В. Aksenov, N. A. Аксенов, Н. А. Aksenova, I. V. Аксенова, И. В.
author_sort	Strelkov, V. D.
title	Mannich Reaction Involving 6-Amino-4-methyl-2-(thio)oxo-1,2-dihydropyridine-3,5-dicarbonitriles
title_short	Mannich Reaction Involving 6-Amino-4-methyl-2-(thio)oxo-1,2-dihydropyridine-3,5-dicarbonitriles
title_full	Mannich Reaction Involving 6-Amino-4-methyl-2-(thio)oxo-1,2-dihydropyridine-3,5-dicarbonitriles
title_fullStr	Mannich Reaction Involving 6-Amino-4-methyl-2-(thio)oxo-1,2-dihydropyridine-3,5-dicarbonitriles
title_full_unstemmed	Mannich Reaction Involving 6-Amino-4-methyl-2-(thio)oxo-1,2-dihydropyridine-3,5-dicarbonitriles
title_sort	mannich reaction involving 6-amino-4-methyl-2-(thio)oxo-1,2-dihydropyridine-3,5-dicarbonitriles
publishDate	2023
url	https://dspace.ncfu.ru/handle/20.500.12258/25524
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Mannich Reaction Involving 6-Amino-4-methyl-2-(thio)oxo-1,2-dihydropyridine-3,5-dicarbonitriles

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