Кафедра фармації та технології органічних речовин (ФтаТОР)

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ENG: Department of Pharmacy and Technology of Organic Substances

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    Synthesis of N-Acyloxy-1-(Dimethoxyphosphoryloxy)Benzimidates from N-Acyloxy-N-Chlorobenzamides
    (Oles Honchar Dnipro National University, Dnipro, 2025) Shtamburg, Vasiliy G.; Klots, Evgeniy A.; Shtamburg, Victor V.; Anishchenko, Andrey A.; Shishkina, Svitlana V.; Mazepa, Alexander V.; Kravchenko, Svetlana V.
    ENG: Aim. The objective of this research was to investigate the potential interaction between N-acyloxy-N-chlorobenzamides and trialkyl phosphites, along with the characterization of the resulting products' structures. Methods. Employing techniques such as 1H, 31P and 13C NMR spectroscopy, mass spectrometry, and single crystal X-ray diffraction, we have proved that the reaction of N-acyloxy-N-chlorobenzamides with trimethyl phosphite in diethyl ether produces N-acyloxy-1-(dimethoxyphosphoryloxy)benzimidates. Our research demonstrates that the reaction between N-acyloxy-N-chlorobenzamides and trialkyl phosphites offers a novel approach to synthesize Z-N-acyloxy-1-(dialkoxyphosphoryloxy)benzimidates. This discovery unveils a significant chemical transformation of N-acyloxy-N-chlorobenzamides. The structure of N-acyloxy-1-(dimethoxyphosphoryloxy)benzimidates has been confirmed by 1H, 31P and 13C NMR spectroscopy, mass spectrometry, and XRD study. The study of the N-(4-nitrobenzoyloxy)-1-(dimethoxyphosphoryloxy)benzimidate structure has revealed that the N-(4-nitrobenzoyloxy)-1-(dimethoxyphosphoryloxy)benzimidate is the Z-isomer, with the dimethoxyphosphoryloxy moiety and the N-4-nitrobenzoyloxy group being cis-oriented to the N=C double bond. The ether moiety and the N=C double bond are coplanar, while the dimethoxyphosphoryl substituent is orthogonal to the plane of the N=C double bond. The interaction of N-acyloxy-N-chlorobenzamides with trimethyl phosphite has led to a new synthesis of Z-N-acyloxy-1-(dialkoxyphosphoryloxy)benzimidates. The new chemical properties of N-acyloxy-N-chlorobenzamides have been established. The X-ray study of Z-N-4-nitrobenzoyoxy-1-benzimidate has demonstrated the peculiarities of its structure. Notably, an intriguing phenomenon of nitrogen-to-oxygen migration of the dimethoxyphosphoryl group has been observed.