RAS Chemistry & Material ScienceЖурнал органической химии Russian Journal of Organic Chemistry

  • ISSN (Print) 0514-7492
  • ISSN (Online) 3034-6304

Synthesis and Chemical Properties of Derivatives of E-3-[3-(2,5-Dihydro-2,5-dioxo-1H-pyrrole-1-yl)phenyl]propenoic Acid

PII
S30346304S0514749225020022-1
DOI
10.7868/S3034630425020022
Publication type
Article
Status
Published
Authors
Volume/ Edition
Volume 61 / Issue number 2
Pages
133-140
Abstract
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.
Keywords
м-аминокоричная кислота 2-бромметил-1,1-дихлорциклопропан малеиновый ангидрид малеинимиды сукцинимиды масс-спектрометрия ИК и ЯМР 1Н спектроскопия
Date of publication
26.12.2024
Year of publication
2024
Number of purchasers
0
Views
22

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