Direct Synthesis of Deuterium-Labeled O -, S -, N-Vinyl Derivatives from Calcium Carbide

Maria S. Ledovskaya, Vladimir V. Voronin, Konstantin S. Rodygin, Alexandra V. Posvyatenko, Ksenia S. Egorova, Valentine P. Ananikov

Research output: Contribution to journalArticlepeer-review

17 Scopus citations

Abstract

A novel methodology for the preparation of trideuterovinyl derivatives of high purity directly from alcohols, thiols, and NH-compounds was developed. Commercially available calcium carbide and D 2 O acted as a D 2 -acetylene source, and DMSO- d 6 was used to complete the formation of the D 2 C=C(D)-X fragment (X = O, S, N). Polymerization of a selected trideuterovinylated compound showed a very promising potential of these substances in the synthesis of labeled polymeric materials. Biological activity of the synthesized trideuterovinyl derivatives was evaluated and the results indicated a significant increase of cytotoxicity upon deuteration.

Original languageEnglish
Pages (from-to)3001-3013
JournalSynthesis (Germany)
Volume51
Issue number15
DOIs
StatePublished - 1 Jan 2019

Scopus subject areas

  • Catalysis
  • Organic Chemistry

Keywords

  • calcium carbide
  • deuterated drugs
  • deuteration
  • deuterium labeling
  • vinylation
  • H/D EXCHANGE
  • HECK REACTIONS
  • CLAISEN REARRANGEMENT
  • ETHERS
  • METABOLISM
  • CYCLOADDITION REACTION
  • ACETALDEHYDE
  • ARYL CHLORIDES
  • METATHESIS

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