1,2,5-Selenadiazolo[3,4-b]pyrazines: synthesis from 3,4-Diamino-1,2,5-selenadiazole and Generation of Persistent Radical Anions

Lidia S. Konstantinova, Irina E. Bobkova, Yulia V. Nelyubina, Elena A. Chulanova, Irina G. Irtegova, Nadezhda V. Vasilieva, Paula Sanz Camacho, Sharon Elizabeth Ashbrook, Guoxiong Hua, Alexandra Martha Zoya Slawin, J Derek Woollins, Andrey V. Zibarev, Oleg A. Rakitin

Research output: Contribution to journalArticlepeer-review

21 Citations (Scopus)

Abstract

Synthesis of 3,4-disubstituted and fused 1,2,5-selenadiazolo[3,4-b]pyrazines via previously unknown 3,4-diamino-1,2,5-selenadiazole has been achieved in moderate to high yields. The compounds synthesized were characterized by elemental analysis, MS and multinuclear (1H, 13C and 77Se) NMR, and the structures of 3,4-diamino-1,2,5-selenadiazole, 5,6-dimethyl[1,2,5]selenadiazolo[3,4-b]pyrazine and 5-phenyl[1,2,5]selenadiazolo[3,4-b]pyrazine were confirmed by X-ray diffraction. Electrochemical reduction of 5,6-R2-1,2,5-selenadiazolo[3,4-b]pyrazines (R = Me, Ph) into persistent radical anions (RAs) was studied by cyclic voltammetry and the RAs were characterized by EPR spectroscopy combined with DFT calculations
Original languageEnglish
Pages (from-to)5585-5593
Number of pages9
JournalEuropean Journal of Organic Chemistry
Volume2015
Issue number25
Early online date23 Jul 2015
DOIs
Publication statusPublished - Sept 2015

Keywords

  • Synthesis
  • [1,2,5]selenadiazolo[3,4-b]pyrazines
  • α- diketones
  • 3,4-diamino-1,2,5-selenadiazole
  • Cyclic voltammetry
  • EPR spectroscopy
  • DFT calculations
  • X-ray diffraction

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