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

doi:10.1248/cpb.42.739

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 journal › Article › peer-review

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 language	English
Pages (from-to)	739-741
Number of pages	3
Journal	Chemical and Pharmaceutical Bulletin
Volume	42
Issue number	3
DOIs	https://doi.org/10.1248/cpb.42.739
Publication status	Published - 1994 Jan 1
Externally published	Yes

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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10.1248/cpb.42.739

Cite this

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

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.",

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",

author = "Jun Toda and Masaharu Seki and Kazuko Amano and Taichi Oyama and Takehiro Sano and Fumiyuki Kiuchi and Yoshisuke Tsuda",

year = "1994",

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doi = "10.1248/cpb.42.739",

language = "English",

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journal = "Chemical and Pharmaceutical Bulletin",

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T1 - Rearrangement of 2,3-dioxo-1,4-oxazines to 4,5-dioxooxazoles in the reaction with dimethylsulfoxonium methylide

AU - Toda, Jun

AU - Seki, Masaharu

AU - Amano, Kazuko

AU - Oyama, Taichi

AU - Sano, Takehiro

AU - Kiuchi, Fumiyuki

AU - Tsuda, Yoshisuke

PY - 1994/1/1

Y1 - 1994/1/1

N2 - 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.

AB - 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.

KW - 2,3-dioxo-2,3-dihydro-4H-1,4-oxazine

KW - 4,5-dioxo-2,3,4,5-tetrahy-drooxazole

KW - dimethylsulfoxonium methylide

KW - methylenation

KW - ring contraction

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

Abstract

Keywords

ASJC Scopus subject areas

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