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

J. Toda, M. Seki, K. Amano, T. Oyama, T. Sano, Fumiyuki Kiuchi, Y. Tsuda

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Reaction of 2,3-dioxo-2,3-dihydro-4H-1,4-oxazines 2a-e with dimethylsulfoxonium methylide introduced an exomethylene group with concomitant ring contraction to give 4,5-dioxo-2,3,4,5-tetrahydrooxazoles 3a- e in moderate yields. Mechanism of this unusual reaction was discussed.

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

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Oxazines
dimethylsulfoxonium methylide
oxazine 1

ASJC Scopus subject areas

  • Chemistry(all)
  • Organic Chemistry
  • Drug Discovery
  • Pharmacology

Cite this

Rearrangement of 2,3-dioxo-1,4-oxazines to 4,5-dioxooxazoles in the reaction with dimethylsulfoxonium methylide. / Toda, J.; Seki, M.; Amano, K.; Oyama, T.; Sano, T.; Kiuchi, Fumiyuki; Tsuda, Y.

In: Chemical and Pharmaceutical Bulletin, Vol. 42, No. 3, 1994, p. 739-741.

Research output: Contribution to journalArticle

Toda, J. ; Seki, M. ; Amano, K. ; Oyama, T. ; Sano, T. ; Kiuchi, Fumiyuki ; Tsuda, Y. / Rearrangement of 2,3-dioxo-1,4-oxazines to 4,5-dioxooxazoles in the reaction with dimethylsulfoxonium methylide. In: Chemical and Pharmaceutical Bulletin. 1994 ; Vol. 42, No. 3. pp. 739-741.
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AU - Seki, M.

AU - Amano, K.

AU - Oyama, T.

AU - Sano, T.

AU - Kiuchi, Fumiyuki

AU - Tsuda, Y.

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