Tricarbonylmethane acylhydrazones: Reactions under acylating conditions and formation of fused isoxazole derivatives with concomitant NN bond cleavage

László Somogyi, Pál Sohár

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

Reactivity of 3‐(1‐acylhydrazonoethyl)‐2H‐pyran‐2‐ones 1a–k and 4a–d towards various acetylating agents and nitrous acid, respectively, is studied. Treatment of dehydroacetic acid (DHA) (thio)acylhydrazones 1a, c, f with Ac2O/Et3N afforded the 3‐(1‐triacetylhydrazinoethenyl) derivative 3a. The analogous coumarin derivative 5 was obtained by treatment of acetylhydrazone 4a with AcCl/PhNMe2. With concomitant N–N bond cleavage acylhydrazones 1c–f were converted to the pyrano‐isoxazole 6 by treatment with NaNO2/AcOH whereas coumarin derivative 4d was converted to the imine 4e.

Original languageEnglish
Pages (from-to)1903-1906
Number of pages4
JournalLiebigs Annalen
Volume1995
Issue number10
DOIs
Publication statusPublished - Sep 22 1995

Keywords

  • Coumarins
  • Dehydroacetic acid (DHA)
  • Hydrazones
  • Isoxazoles

ASJC Scopus subject areas

  • Chemistry(all)

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