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

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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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ACKNOWLEDGMENTS

The experiments were performed using the equipment of Scientific-Education Center “Diagnostics of Structure and Properties of Nanomaterials” of Kuban State University and Center for Collective Usage “Surface and Novel Materials” of Udmurt Federal Research Center, Ural Branch of RAS.

Funding

This study was financially supported by Kuban Science Foundation in the scope of the science project no. MFI-20.1-26/20 (application no. MFI-20.1/45) as well as by North Caucasus Federal University (interdisciplinary project “Synthesis and Antidote Activity with Respect to Herbicide 2,4-D of Heterocyclic Derivatives of Methylene-Active Nitriles,” V.D. Strelkov and I.V. Aksenova) in the framework of the program for strategic academic leadership “PRIORITET-2030.” Investigation of the anticorrosion activity was performed according to the research plan no. 121030100002-0 (Ministry of Science and Higher Education of Russia). The experiments using X-ray photoelectron spectroscopy were supported by Ministry of Science and Higher Education of Russia (agreement no. 075-15-2021-1351; F.F. Chausov, N.V. Lomova, I.S. Kazantseva, and N.Yu. Isupov).

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Authors and Affiliations

  1. Kuban State University, 350040, Krasnodar, Russia

    A. O. Panaetov, V. D. Strelkov & V. V. Dotsenko

  2. North Caucasus Federal University, 355009, Stavropol, Russia

    V. D. Strelkov, V. V. Dotsenko, N. A. Aksenov & I. V. Aksenova

  3. Udmurt Federal Research Center, Ural Branch of the Russian Academy of Sciences, 426067, Izhevsk, Russia

    F. F. Chausov, N. V. Lomova, I. S. Kazantseva & N. Yu. Isupov

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  1. A. O. Panaetov
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Panaetov, A.O., Strelkov, V.D., Dotsenko, V.V. et al. Mannich Reaction Involving 6-Amino-4-methyl-2-(thio)oxo-1,2-dihydropyridine-3,5-dicarbonitriles. Russ J Gen Chem 93, 1655–1668 (2023). https://doi.org/10.1134/S1070363223070046

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  • DOI: https://doi.org/10.1134/S1070363223070046

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