N-N(+) Bond-Forming Intramolecular Cyclization of O-Tosyloxy β-Aminopropioamidoximes and Ion Exchange Reaction for the Synthesis of 2-Aminospiropyrazolilammonium Chlorides and Hexafluorophosphates

Kayukova, L.; Vologzhanina, A.; Dorovatovskii, P.; Yergaliyeva, E.; Asem, U.; Aidana, D.

Авторы: Kayukova Lyudmila, Vologzhanina Anna, Dorovatovskii Pavel, Yergaliyeva Elmira, Asem Uzakova, Aidana Duisenali
Журнал: International Journal of Molecular Sciences
Том: 24
Номер: 14
Год издания: 2023
Издательство: MDPI
Местоположение издательства: Basel, Switzerland
Номер статьи: 11315
DOI: 10.3390/ijms241411315
Аннотация: Our research area is related to the spiropyrazolinium-containingcompounds, which are insufficiently studied compared with pyrazoline-containing compounds. Nitrogen-containing azoniaspiromolecules have also been well studied. In drug design and other areas, they are a priori important structures, since rigid spirocyclic scaffolds with the reduced conformational entropy are able to organize a closely spaced area. Azoniaspirostructures are currently of wide practical interest as ionic liquids, current sources (membranes), structure-directing agents in organocatalysis, and in the synthesis of ordered ceramics. Our goal was the synthesis of 2-aminospiropyrazolilammonium chlorides and hexafluorophosphates. Our methodology is based on the tosylation of β-aminopropioamidoximes with six-membered N-heterocycles (piperidine, morpholine, thiomorpholine, and phenylpiperazine) at the β-position. 2-Aminospiropyrazolilammonium chlorides and hexafluorophosphates were obtained by the reaction of double ion substitution in the reaction of toluenesulfonates of 2-aminospiropyrazolinium compounds with an ethereal solution of HCl in ethanol and with ammonium hexafluorophosphate in ethanol in quantitative yields of 55–97%. The physicochemical characteristics of the synthesized compounds and their IR and NMR spectra are presented. The obtained salts were additionally characterized by the single-crystal XRD analysis. The presence of both axial and equatorial conformations of spirocations in solids was confirmed. 2-Aminospiropyrazolilammonium chlorides and hexafluorophosphates have weak in vitro antimicrobial activity on Gram-positive and Gram-negative bacterial lines.
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№	Имя	Описание	Имя файла	Размер	Добавлен
1.	Полный текст		ijms-Kayukova.pdf	2,7 МБ	11 июля 2023 [VologzhaninaAV]
2.	экспертное заключение		230717132203_0001.pdf	209,8 КБ	17 июля 2023 [VologzhaninaAV]

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N-N(+) Bond-Forming Intramolecular Cyclization of O-Tosyloxy β-Aminopropioamidoximes and Ion Exchange Reaction for the Synthesis of 2-Aminospiropyrazolilammonium Chlorides and Hexafluorophosphatesстатья

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