Synthesis of 4,5-dihydroisoxazole derivatives of maleopimaric acid by 1,3-dipolar cycloaddition reaction between its allyl derivatives and aromatic nitrile oxides

Vafina, G. F.; Mukhamed’yanova, A. A.; Khanova, M. D.; Спирихин, Л. В.

doi:10.1007/s10593-018-2352-5

Cited by 7 publications

(1 citation statement)

References 7 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Были получены N-(1-нафтил-, хинолин-8-ил)имиды метиловых эфиров малеопимаровой кислоты и исследованы кинетические параметры взаимопревращения атропоизомеров этих соединений [9]. С использованием разработанного нами ранее [10] аллилового эфира малеопимаровой кислоты получены 4,5-дигидроизоксазолсодержащие производные малеопимаровой кислоты, проявляющие антимикробную и фунгицидную активность [11].…”

unclassified

Synthesis and properties of maleopimaric acid amides, imides and imidoamides with arylisoxazole and quinoline fragments

Bei

Yuvchenko

Поткин

et al. 2021

Vescì Akademìì navuk Belarusì. Seryâ himičnyh navuk

View full text Add to dashboard Cite

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.

show abstract

unclassified