Synthesis of highly substituted 2H-azirine-2-carboxylates via 3-azido-4-oxobut-2-enoates

T. Patonay, J. Jekó́, Éva Juhász-Tóth

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

Phenacyl azides have been transformed into ethyl 4-aryl-3-azido-2-methyl-4- oxobut-2-enoates by base-induced coupling of the starting α-azido ketone with ethyl pyruvate followed by elimination of methanesulfonic acid from the mesylate generated in situ from the labile aldol-type intermediates ethyl 4-aryl-3-azido-2-hydroxy-2-methyl-4-oxobutanoates. Thermolysis of ethyl 4-aryl-3-azido-2-methyl-4-oxobut-2-enoates resulted in the formation of the hitherto unknown 3-aroyl-2-ethoxycarbonyl-2-methyl-2H-azirines.

Original languageEnglish
Pages (from-to)1441-1448
Number of pages8
JournalEuropean Journal of Organic Chemistry
Issue number8
DOIs
Publication statusPublished - Mar 2008

Fingerprint

Azirines
pyruvates
Thermolysis
Mesylates
Azides
Ketones
ketones
carboxylates
elimination
acids
synthesis
ethyl pyruvate
methanesulfonic acid
3-hydroxybutanal

Keywords

  • Azides
  • Azirines
  • C-C coupling
  • Nitrenes
  • Thermolysis

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry

Cite this

Synthesis of highly substituted 2H-azirine-2-carboxylates via 3-azido-4-oxobut-2-enoates. / Patonay, T.; Jekó́, J.; Juhász-Tóth, Éva.

In: European Journal of Organic Chemistry, No. 8, 03.2008, p. 1441-1448.

Research output: Contribution to journalArticle

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