Synthesis and chemical properties of derivatives of  E -3-[3-(2,5-dihydro-2,5-dioxo-1 Н -pyrrole-1-yl)phenyl]propenoic acid

O. A. Kolyamshin; Колямшин Олег Актарьевич; Yu. N. Mitrasov; Митрасов Юрий Никитич; V. A. Danilov; Данилов Владимир Александрович; A. A. Avruyskaya; Авруйская Анжелика Анатольевна; Yu. Y. Pylchikova; Пыльчикова Юлия Юрьевна

doi:10.31857/S0514749225020022

Synthesis and chemical properties of derivatives of E-3-[3-(2,5-dihydro-2,5-dioxo-1Н-pyrrole-1-yl)phenyl]propenoic acid

作者: Kolyamshin O.A.¹, Mitrasov Y.N.², Danilov V.A.¹, Avruyskaya A.A.², Pylchikova Y.Y.¹
隶属关系:
1. Chuvash State University named after I.N. Ulyanov
2. Chuvash State Pedagogical University named after I.Y. Yakovlev
期: 卷 61, 编号 2 (2025)
页面: 133-140
栏目: Articles
URL: https://freezetech.ru/0514-7492/article/view/684302
DOI: https://doi.org/10.31857/S0514749225020022
EDN: https://elibrary.ru/DFWZYP
ID: 684302

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By the reaction of m-aminocoric acid with maleic anhydride in an acetone medium, Z-4-{3-(E-2-carboxyethenyl)phenylamino}-4-oxo-2-butenic acid was synthesized, intramolecular cyclization of which in the presence of p-toluene sulfonic acid E-3-[3-(2,5-dihydro-2,5-dioxo-1H-pyrrole-1-yl)phenyl]propenic acid. It has been shown that the interaction of the potassium salt of m-aminocortic acid with 2-bromomethyl-1,1-dichlorocyclopropane proceeds chemoselectively while maintaining a three-membered cycle and leads to the formation of E-2,2-dichlorocyclopropylmethyl-3-(3-aminophenyl)propenoate, on the basis of which, under the sequential action of maleic and acetic anhydrides in the presence of sodium acetate, E-2,2-dichlorocyclopropylmethyl-3-[3-(2,5-dihydro-2,5-dioxo-1H-pyrrole-1-yl)phenyl]propenoate was obtained. It was found that under the action of secondary amines, it reacts with aza-Michael to form 2,2-dichlorocyclopropylmethyl-3-[3-(3-R₂N-2,5-dioxo-2,3,4,5-tetrahydro-1H-pyrrol-1-yl)phenyl]propenoates.

关键词

m-aminocorric acid, 2-bromomethyl-1, 1-dichlorocyclopropane, maleic anhydride, maleinimides, succinimides, mass spectrometry, IR and 1H NMR spectroscopy

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参考

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