Isoxazole to oxazole: a mild and unexpected transformation

3-Aryltetrahydrobenzisoxazoles prepared en route to the coleophomone natural products and analogues, were found to undergo a remarkable base-mediated rearrangement to 2-aryltetrahydrobenzoxazoles. The scope of this unprecedented, facile transformation was probed: a range of analogues was produced, a...

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Veröffentlicht in:	Chemical communications (Cambridge, England) England), 2015-01, Vol.51 (6), p.1112-1115
Hauptverfasser:	Jones, Raymond C F, Chatterley, Alexander, Marty, Romain, Owton, W Martin, Elsegood, Mark R J
Format:	Artikel
Sprache:	eng
Schlagworte:	Crystallography, X-Ray Herbicides Heterocyclic Compounds, 4 or More Rings - chemistry Isoxazoles - chemistry Molecular Structure Natural products Oxazole Oxazoles - chemistry Synthesis Transformations
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Beschreibung
Zusammenfassung:	3-Aryltetrahydrobenzisoxazoles prepared en route to the coleophomone natural products and analogues, were found to undergo a remarkable base-mediated rearrangement to 2-aryltetrahydrobenzoxazoles. The scope of this unprecedented, facile transformation was probed: a range of analogues was produced, a mechanism proposed, and an application demonstrated by synthesis of a known herbicidal compound.
ISSN:	1359-7345 1364-548X
DOI:	10.1039/c4cc07999j