Rearrangement of 2,3-dioxo-1,4-oxazines to 4,5-dioxooxazoles in the reaction with dimethylsulfoxonium methylide

Jun Toda, Masaharu Seki, Kazuko Amano, Taichi Oyama, Takehiro Sano, Fumiyuki Kiuchi, Yoshisuke Tsuda

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Reaction of 2,3-dioxo-2,3-dihydro-4//-l,4-oxazines 2a-e with dimethylsulfoxonium methylide introduced an exo-methylene group with concomitant ring contraction to give 4,5-dioxo-2,3,4,5-tetrahydrooxazoles 3a-e in moderate yields Mp.rhanism of this unusual reaction was discussed.

Original languageEnglish
Pages (from-to)739-741
Number of pages3
JournalChemical and Pharmaceutical Bulletin
Volume42
Issue number3
DOIs
Publication statusPublished - 1994 Jan 1
Externally publishedYes

Keywords

  • 2,3-dioxo-2,3-dihydro-4H-1,4-oxazine
  • 4,5-dioxo-2,3,4,5-tetrahy-drooxazole
  • dimethylsulfoxonium methylide
  • methylenation
  • ring contraction

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

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