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0221U106834,
0116U008798
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Development of the synthesis methods for new types of fluorinated organic compounds as starting products for the synthesis of potentially bioactive substances
Shermolovich Yurii H., Доктор хімічних наук
21-12-2021
Institute of Organic Chemistry NAS of Ukraine
The reactions of sulfur tetrafluoride with esters of α-aminothio acids were studied and a new type of dialkylamines containing α,α-difluorosulfide fragment was obtained. The reaction of α- and β-amino acid esters derivatives with sulfur tetrafluoride proved to be a good method for obtaining a new type of difluoroanhydrides of imidosulfuric acids, which react with N-trimethylsilyl derivatives of primary amines to form N-sulfide diimides. The reaction with N-trimethylsilylmorpholine leads to the formation of aldimines and ketimines containing the fragment =N-S-NR2. For the first time, a convenient synthetic method has been developed for the soft conversion of aryl and heteryl tetrafluorochloropersulfuranes to pentafluoropersulfurans using a stoichiometric amount of HgO and HF or PPHF as the second component of the fluorinating reagent. X-ray diffraction studies of the 2-SF5-benzothiazole and 2-SF5-pyrimidine molecules showed the presence of a deformed octahedral environment of sulfur atoms and elongation of the C-S bond for the pyrimidine derivative compared to the mean values for such compounds. A method for the synthesis of pyrimidine-4(3H)-ones with groups SCF3, SOCF3 and SO2CF3 at position 5 of the pyrimidine ring has been developed. A study of the difluoromethylation reaction of indole derivatives was performed and it was shown that the thermal and hydrolytic stability of N-difluoromethylindoles depends on the electronic nature of the substituents in the heterocyclic ring. Preparative methods for the synthesis of functionalized azoles containing chiral highly lipophilic fluorine-containing substituent - 1,1-difluoro-2-fluoro-2- (trifluoromethoxy)-ethyl group have been found. It is shown that products are thermally and hydrolytically stable, which makes them promising synthons for obtaining biologically active compounds.
Babadzhanova Lesia A
Boiko Volodymir M
Borodkin Yaroslav S
Guzyr Olexandr I
Zasukha Sergіy V
Kamіns’ka Olena I
Kirij Nataliia V
Kolesnik Natalіya P
Kremlev Michail M
Markіtanov Yurii M
Mikhaylichenko Sergіy S
Mushta Olexii I
Orlova Raisa K
Pavlenko Nataliia V
Petko Kiril I
Sіry Sergіy A
Sokolenko Liubov V
Sokolenko Taras M
Timoshenko Vadim M
Filatov Andrey A
Yagupolskii Yurii L
2021-12-21
Updated: 2025-12-07
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