vestichИзвестия Национальной академии наук Беларуси. Серия химических наукProceedings of the National Academy of Sciences of Belarus, Chemical Series1561-83312524-2342The Republican Unitary Enterprise Publishing House "Belaruskaya Navuka"10.29235/1561-8331-2021-57-4-424-430vestich-686Research ArticleОРГАНИЧЕСКАЯ ХИМИЯORGANIC CHEMISTRYСинтез и свойства амидов, имидов и имидоамидов малеопимаровой кислоты с арилизоксазольным и хинолиновым фрагментамиSynthesis and properties of maleopimaric acid amides, imides and imidoamides with arylisoxazole and quinoline fragmentsБейМ. П.BeiM. P.

Бей Максим Петрович – канд. хим. наук, вед. науч. сотрудник

ул. Ф. Скорины, 36, 220141, Минск, Республика Беларусь

Maksim P. Bei – Ph. D. (Chemistry), Leading Researcher

36, F. Skoriny str., 220141, Minsk, Republic of Belarus

beymaksim@gmail.comЮвченкоА. П.YuvchenkoA. P.

Ювченко Анатолий Петрович – канд. хим. наук, ст. науч. сотрудник

ул. Ф. Скорины, 36, 220141, Минск, Республика Беларусь

Anatolij P. Yuvchenko – Ph. D. (Chemistry), Senior Researcher

36, F. Skoriny str., 220141, Minsk, Republic of Belarus

mixa@ichnm.byПоткинВ. И.PotkinV. I.

Поткин Владимир Иванович – член-корреспондент, д-р хим. наук, профессор, зав. отделом

ул. Сурганова, 13, 220072, Минск, Республика Беларусь

Vladimir I. Potkin – Corresponding Member of the National Academy of Sciences of Belarus, D. Sc. (Chemistry), Professor, Head of the Department

13, Surganov str., 220072, Minsk, Republic of Belarus

potkin@ifoch.bas-net.byПеткевичС. К.PetkevichS. K.

Петкевич Сергей Константинович – канд. хим. наук, вед. науч. сотрудник

ул. Сурганова, 13, 220072, Минск, Республика Беларусь

Sergey K. Petkevich – Ph. D. (Chemistry), Leading Researcher

13, Surganov str., 220072, Minsk, Republic of Belarus

petkevich@ifoch.bas-net.byИнститут химии новых материалов Национальной академии наук БеларусиInstitute of Chemistry of New Materials of the National Academy of Science of BelarusИнститут физико-органической химии Национальной академии наук БеларусиInstitute of Physical Organic Chemistry of the National Academy of Sciences of Belarus202103122021574424430Copyright © Бей М.П., Ювченко А.П., Поткин В.И., Петкевич С.К., 20212021Бей М.П., Ювченко А.П., Поткин В.И., Петкевич С.К.Bei M.P., Yuvchenko A.P., Potkin V.I., Petkevich S.K.Данная работа распространяется под лицензией Creative Commons Attribution 4.0.This work is licensed under a Creative Commons Attribution 4.0 License.https://vestichem.belnauka.by/jour/article/view/686

Разработан метод синтеза N-(5-арилизоксазол-3-ил)амидов малеопимаровой кислоты взаимодействием хлорангидрида малеопимаровой кислоты и 3-амино-5-фенил(4-метилфенил)изоксазолов. На основе полученных амидов синтезированы N’-бутил-, N’-(2-гидроксиэтил)имиды N-(5-арилизоксазол-3-ил)амидов малеопимаровой кислоты. Взаимодействием малеопимаровой кислоты и 8-аминохинолина в кипящем толуоле впервые синтезирован гетероциклический имид – N-(хинолин-8-ил)имид малеопимаровой кислоты с выходом 97,1 %. Установлено, что при кипячении в толуоле 8-аминохинолина и канифольно-малеинового аддукта, получаемого обработкой смоляных кислот канифоли малеиновым ангидридом и содержащего не менее 50 % малеопимаровой кислоты, также происходит образование N-(хинолин-8-ил)имида малеопимаровой кислоты с выходом 52,5 % (в расчете на массу канифольно-малеинового аддукта). Методами ИК- и ЯМР 1Н спектроскопии и масс-спектрометрии показано, что N-(хинолин-8-ил)имид малеопимаровой кислоты представляет собой смесь двух диастереомерных атропоизомеров в соотношении 1:0,40. Произведена оценка биологической активности ряда полученных соединений. Установлено, что N-(5-(4-метилфенил)изоксазолил-3)амид малеопимаровой кислоты обладает закручивающей способностью (26,0 мкм-1) и может быть использован в качестве хиральной добавки к нематической ЖК-матрице для получения хиральных ЖК-композиций.

The method for maleopimaric acid N-(5-arylisoxazol-3-yl)amides synthesis has been developed by reaction of maleopimaric acid chloride with 3-amine-5-phenyl(4-methylphenyl)isoxazoles. N’-butyl-, N’-(2-hydroxyethyl)imides of maleopimaric acid N-(5-arylisoxazol-3-yl)amides were prepared. Heterocyclic imide – maleopimaric acid N-(quinolin-8-yl) imide was prepared by reaction of maleopimaric acid and 8-aminoquinoline in toluene at reflux in 97.1 % yield. It was established that refluxing of toluene solution of 8-aminoquinoline and maleated rosin, prepared by treatment of rosin with maleic anhydride and containing at least 50 % of maleopimaric acid, leads to the formation of maleopimaric acid N-(quinolin-8-yl)imide in 52.5 % yield (based on weight of maleated rosin). It was found by the methods of IR-, 1H NMR spectroscopy and mass-spectrometry that maleopimaric acid N-(quinolin-8-yl)imide consists of two diastereomeric atropisomers at 1:0.40 ratio. The biological properties of the prepared compounds were studied. It was established that maleopimaric acid N-(5-(4-methylphenyl)isoxazol-3-yl)amide possesses rotatory power (26 mkm-1) and may be used as chiral dopant to nematic LC for preparation of chiral LC-compositions.

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The authors declare that there are no conflicts of interest present.