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Lyudmila Kayukova Anna Vologzhanina Pavel Dorovatovskii Gulnur Baitursynova Elmira Yergaliyeva Ayazhan Kurmangaliyeva Zarina Shulgau Sergazy Adekenov Zhanar Shaimerdenova Kydymolla Akatan 《Molecules (Basel, Switzerland)》2022,27(7)
Nitrobenzenesulfochlorination of β-aminopropioamidoximes leads to a set of products depending on the structure of the initial interacting substances and reaction conditions. Amidoximes, functionalized at the terminal C atom with six-membered N-heterocycles (piperidine, morpholine, thiomorpholine and phenylpiperazine), as a result of the spontaneous intramolecular heterocyclization of the intermediate reaction product of an SN2 substitution of a hydrogen atom in the oxime group of the amidoxime fragment by a nitrobenzenesulfonyl group, produce spiropyrazolinium ortho- or para-nitrobenzenesulfonates. An exception is ortho-nitrobenzenesulfochlorination of β-(thiomorpholin-1-yl)propioamidoxime, which is regioselective at room temperature, producing two spiropyrazolinium salts (ortho-nitrobezenesulfonate and chloride), and regiospecific at the boiling point of the solvent, when only chloride is formed. The para-Nitrobezenesulfochlorination of β-(benzimidazol-1-yl)propioamidoxime, due to the reduced nucleophilicity of the aromatic β-amine nitrogen atom, is regiospecific at both temperatures, and produces the O-para-nitrobenzenesulfochlorination product. The antidiabetic screening of the new nitrobezenesulfochlorination amidoximes found promising samples with in vitro α-glucosidase activity higher than the reference drug acarbose. 1H-NMR spectroscopy and X-ray analysis revealed the slow inversion of six-membered heterocycles, and experimentally confirmed the presence of an unfavorable stereoisomer with an axial N–N bond in the pyrazolinium heterocycle. 相似文献
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E. M. Suleimen K. Van Hecke Z. A. Ibatayev K. Akatan 《Journal of Structural Chemistry》2018,59(2):344-346
The crystal structure of 1,2-bis(acetoxymethyl)-o-carborane is determined by the X-ray crystallographic analysis. 相似文献
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