Catalytic aza-Wittig Cyclizations for Heteroaromatic Synthesis

Catalytic aza-Wittig Cyclizations for Heteroaromatic Synthesis

The first examples of heterocycle synthesis by iminophosphorane formation/intramolecular aza-Wittig cyclizations that are catalytic in the organophosphorus component are reported. The reaction has been demonstrated in the synthesis of both azine (phenanthridine) and azole (benzoxazole) heterocycles....

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Veröffentlicht in:Organic letters 2008-06, Vol.10 (12), p.2589-2591
Hauptverfasser: Marsden, Stephen P, McGonagle, Alison E, McKeever-Abbas, Ben
Format: Artikel
Sprache:eng
Schlagworte:
Aza Compounds - chemistry
Benzoxazoles - chemical synthesis
Benzoxazoles - chemistry
Catalysis
Cyclization
Molecular Structure
Spectrophotometry, Infrared
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Zusammenfassung:The first examples of heterocycle synthesis by iminophosphorane formation/intramolecular aza-Wittig cyclizations that are catalytic in the organophosphorus component are reported. The reaction has been demonstrated in the synthesis of both azine (phenanthridine) and azole (benzoxazole) heterocycles. Catalyst loadings down to 1 mol % have been used with little or no loss in reaction efficiency. The intimate involvement of the phosphine oxide in the catalytic cycle has been verified by in situ infrared spectroscopy.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol800921n