Synthesis of 3,4-disubstituted 2,5-dihydropyrrol-1-yloxyl spin label reagents

Cecília P. Sár, J. Jekó́, K. Hideg

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

4-Alkyl(or aryl)-3-ethoxycarbonyl-2,5-dihydro-1H-pyrrol-1-yloxyl radicals 5a-g were prepared in a multistep reaction via base-catalyzed conjugate addition of 2-nitropropane to β-aryl(or -alkyl)-α, β- unsaturated-α-ethoxycarbonyl ketones to give γ-nitro ketones, followed by a cyclization to 3,4-dihydro-2H-pyrrole 1-oxides, dehydrobromination to 2H- pyrrole 1-oxides and then Grignard reaction. The esters 5a-g are versatile synthons for obtaining highly SH-specific allylic iodide 7a,c-g and methylsulfonylthiomethyl 8a-g spin label reagents.

Original languageEnglish
Pages (from-to)1497-1500
Number of pages4
JournalSynthesis
Issue number10
Publication statusPublished - Oct 1998

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Spin Labels
Ketones
Oxides
Labels
Pyrroles
Cyclization
Iodides
Esters
2-nitropropane
delta(1)-pyrroline

Keywords

  • 3,4-disubstituted 2,5-dihydropyrrole nitroxides
  • Nitrones
  • SH-specific spin label reagents

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Synthesis of 3,4-disubstituted 2,5-dihydropyrrol-1-yloxyl spin label reagents. / Sár, Cecília P.; Jekó́, J.; Hideg, K.

In: Synthesis, No. 10, 10.1998, p. 1497-1500.

Research output: Contribution to journalArticle

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