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Monatshefte für Chemie - Chemical Monthly

, Volume 150, Issue 1, pp 85–101 | Cite as

An alternative way to analogues of avenanthramides and their antiradical activity

  • Inese MierinaEmail author
  • Agnese Stikute
  • Anatoly Mishnev
  • Mara Jure
Original Paper
  • 37 Downloads

Abstract

The paper is devoted to the synthesis of arylidene malonic acid monoanilides and cinnamoyl anilines by condensation of malonic acid monoanilides with aromatic aldehydes. The presented synthetic route applies simple, cheap, and commercially available aromatic aldehydes and amines, thus overcoming traditional schemes, which involve derivatives of hydroxycinnamic acids. Besides, a mild and effective pyridine-mediated decarboxylation of carboxylic group at Csp2 in arylidene malonic acid monoanilides leading to cinnamoyl anilines is presented. The structures of obtained selected arylidene derivatives were approved additionally by X-ray analysis. The antiradical properties (2,2-diphenyl-1-picrylhydrazyl and galvinoxyl tests) and structure–activity relationships of the synthesized compounds were studied.

Graphical abstract

Keywords

Aldol condensation Antioxidant Carbonyl compounds Carboxylic acids Cinnamoyl anilines Retro reactions X-ray structure determination 

Notes

Acknowledgements

This work was supported by the European Social Fund within the project “Support for the implementation of doctoral studies at Riga Technical University”. Authors thank to JSC “Olainfarm” for scholarship to Agnese Stikute.

Supplementary material

706_2018_2288_MOESM1_ESM.pdf (5.4 mb)
Supplementary material 1 (PDF 5579 kb)

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Copyright information

© Springer-Verlag GmbH Austria, part of Springer Nature 2018

Authors and Affiliations

  • Inese Mierina
    • 1
    Email author
  • Agnese Stikute
    • 1
  • Anatoly Mishnev
    • 2
  • Mara Jure
    • 1
  1. 1.Institute of Technology of Organic Chemistry, Faculty of Materials Science and Applied ChemistryRiga Technical UniversityRigaLatvia
  2. 2.Latvian Institute of Organic SynthesisRigaLatvia

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