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Synthesis, spectral characteristics, and molecular structure of 2-(2,4-dichlorophenyl)-6-(2-methoxybenzyl)-4-(trichloromethyl)-4H-1,3,5-oxadiazine

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Abstract

This work reports on the synthesis of a new member of the 1,3,5-oxadiazine series—2-(2,4-dichlorophenyl)-6-(2-methoxybenzyl)-4-(trichloromethyl)-4H-1,3,5-oxadiazine. The target product was obtained by eliminating hydrogen sulfide from 2,4-dichloro-N-(2,2,2-trichloro-1-(3-(2-methoxyphenyl)thioureido)ethyl)benzamide under the action of dicyclohexylcarbodiimide. The structures of the synthesized compounds were proved by 1H and 13C NMR, IR spectroscopy, and mass spectrometry data. The mass spectrometric fragmentation of the resulting 1,3,5-oxadiazine under conditions of fast atom bombardment was discussed. In addition, X-ray diffraction studies were carried out for it. In the crystal, the 1,3,5-oxadiazine ring existed in two conformations: a flattened bath (85% occupancy) and a sofa (15% occupancy).

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Authors and Affiliations

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

    Pavlo V. Zadorozhnii, Vadym V. Kiselev, Olha O. Hrek, Aleksandr V. Kharchenko & Oxana V. Okhtina

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  1. Pavlo V. Zadorozhnii
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  2. Vadym V. Kiselev
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  3. Olha O. Hrek
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  4. Aleksandr V. Kharchenko
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  5. Oxana V. Okhtina
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Contributions

P.V.Z.: conceptualization, methodology, writing-original draft, formal analysis, investigation, visualization, project administration; V.V.K.: validation, resources, writing-review and editing; O.O.H.: methodology, formal analysis; A.V.K.: validation, supervision, writing-review and editing; O.V.O.: methodology, formal analysis, investigation.

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Correspondence to Pavlo V. Zadorozhnii.

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Zadorozhnii, P.V., Kiselev, V.V., Hrek, O.O. et al. Synthesis, spectral characteristics, and molecular structure of 2-(2,4-dichlorophenyl)-6-(2-methoxybenzyl)-4-(trichloromethyl)-4H-1,3,5-oxadiazine. Struct Chem 33, 2127–2132 (2022). https://doi.org/10.1007/s11224-022-02024-9

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