Heteroaromatic Decarboxylative Claisen Rearrangement Reactions

Heteroaromatic Decarboxylative Claisen Rearrangement Reactions

ABSTRACT Furan-2-ylmethyl, thien-2-ylmethyl and pyrrol-2-yl­methyl tosylacetates undergo facile decarboxylative Claisen rearrangement upon exposure to N,O-bis(trimethylsilyl)acetamide-potassium acetate to yield the corresponding 2,3-disubstituted heteroaromatic products in good yield. However, for 1...

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Veröffentlicht in:Synthesis (Stuttgart) 2005-12, Vol.2005 (19), p.3279-3282
Hauptverfasser: Craig, Donald, King, N. Paul, Kley, Jörg T., Mountford, David M.
Format: Artikel
Sprache:eng
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Zusammenfassung:ABSTRACT Furan-2-ylmethyl, thien-2-ylmethyl and pyrrol-2-yl­methyl tosylacetates undergo facile decarboxylative Claisen rearrangement upon exposure to N,O-bis(trimethylsilyl)acetamide-potassium acetate to yield the corresponding 2,3-disubstituted heteroaromatic products in good yield. However, for 1-(thien-2-yl)ethyl tosylacetates and substrates derived from 3-(hydroxyalkyl)indoles rearomatisation does not occur.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-2005-918448