Oxidation of dioxopyrroline with m-chloroperbenzoic acid: Selective formation of 2,3-dioxo-1,4-oxazine

Takehiro Sano, Kazuko Amano, Masaharu Seki, Hiroyuki Hirota, Jun Toda, Fumiyuki Kiuchi, Yoshisuke Tsuda

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)

Abstract

Treatment of 4-ethoxycarbonyl-5-phenyl-1H-pyrrole-2,3-diones (1a-1e) and 4-benzoyl-1,5-diphenyl-1H-pyrrole-2,3-dione (1f) with m-chloroperbenzoic acid caused Baeyer-Villiger oxidation to give 2,3-dioxo-1,4-oxazines (2a-2f) in moderate yields, respectively. This conversion of the 1H-pyrrole-2,3-dione into the 2,3-dioxo-1,4-oxazine provides the first synthesis of monocyclic 2,3-dioxo-1,4-oxazine ring system.

Original languageEnglish
Pages (from-to)523-528
Number of pages6
JournalHeterocycles
Volume37
Issue number1
DOIs
Publication statusPublished - 1994 Jan 1
Externally publishedYes

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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