REARRANGEMENT OF 2, 3-DIOXO-1, 4-OXAZINES TO 4, 5-DIOXOOXAZOLES IN THE REACTION WITH DIMETHYLSULFOXONIUM METHYLIDE

Reaction of 2, 3-dioxo-2, 3-dihydro-4H-1, 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. Mechanism of this unusual reaction was discussed.

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Bibliographische Detailangaben
Veröffentlicht in:	Chemical & pharmaceutical bulletin 1994/03/15, Vol.42(3), pp.739-741
Hauptverfasser:	TODA, Jun, SEKI, Masaharu, AMANO, Kazuko, OYAMA, Taichi, SANO, Takehiro, KIUCHI, Fumiyuki, TSUDA, Yoshisuke
Format:	Artikel
Sprache:	eng
Schlagworte:	2, 3-dioxo-2, 3-dihydro-4H-1, 4-oxazine 4, 5-dioxo-2, 3, 4, 5-tetrahydrooxazole Chemistry dimethylsulfoxonium methylide Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms methylenation Organic chemistry Preparations and properties ring contraction
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Beschreibung
Zusammenfassung:	Reaction of 2, 3-dioxo-2, 3-dihydro-4H-1, 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. Mechanism of this unusual reaction was discussed.
ISSN:	0009-2363 1347-5223
DOI:	10.1248/cpb.42.739