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Synthesis of 3,4-dihydro-1,3,5-triazin-2(1H)-one derivatives by recycling 2H-1,3,5-oxadiazine-2,4(3H)-diimines: their spectral characteristics and molecular structure

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Abstract

1,3,5-Triazine derivatives are an important class of six-membered heterocyclic compounds of great interest in medicine, pharmacy, agriculture, polymer, electronics, and other industries. In this paper, we report on the synthesis of 1,3,5-triazine derivatives by the 1,3,5-oxadiazine ring transformation. The reaction was carried out by refluxing the starting 1,3,5-oxadiazines in a methanol-alkaline solution. The reaction products were obtained in 82–88% yields. Their structure was confirmed by 1H and 13C NMR, IR spectroscopy, and mass spectrometry data. X-ray diffraction studies were carried out for one of the representatives of some 1,3,5-oxadiazines and 1,3,5-triazines.

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The online version contains supplementary material and data available at https://doi.org/10.1007/s11224-023-02184-2.

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Funding

The work has been financially supported by the Krzysztof Skubiszewski Foundation (Warsaw, Poland), program “Urgent Aid for the Preservation of the Research Capabilities of Ukraine” and funded project “Synthesis and biological activity of nitrogen-containing heterocyclic compounds based on N-(isothiocyanatoalkyl)carboxamides”, grant # 0000000342.

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  1. Department of Pharmacy and Technology of Organic Substances, Ukrainian State University of Chemical Technology, Gagarin Ave., 8, Dnipro, 49005, Ukraine

    Ihor O. Pokotylo, Pavlo V. Zadorozhnii, Vadym V. Kiselev & Aleksandr V. Kharchenko

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  1. Ihor O. Pokotylo
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  2. Pavlo V. Zadorozhnii
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  3. Vadym V. Kiselev
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I.O.P.: methodology, formal analysis; P.V.Z.: conceptualization, methodology, writing-original draft, formal analysis, investigation, visualization, project administration; V.V.K.: validation, resources, writing-review and editing; A.V.K.: validation, supervision, writing-review and editing.

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Correspondence to Pavlo V. Zadorozhnii.

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Pokotylo, I.O., Zadorozhnii, P.V., Kiselev, V.V. et al. Synthesis of 3,4-dihydro-1,3,5-triazin-2(1H)-one derivatives by recycling 2H-1,3,5-oxadiazine-2,4(3H)-diimines: their spectral characteristics and molecular structure. Struct Chem 34, 2273–2279 (2023). https://doi.org/10.1007/s11224-023-02184-2

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