A Novel Route to 2,3-Pyrazol-1(5H)-ones via Palladium-Catalyzed Carbonylation of 1,2-Diaza-1,3-butadienes

A novel Pd(0)-catalyzed carbonylation of both isolable 1,2-diaza-1,3-butadienes and those generated in situ by extrusion of SO2 and CO2 from heterocyclic precursors is described. The reaction proceeds at room temperature to 110 °C under 1−2 atm of CO to afford 2,3-pyrazol-1(5H)-ones in good to excel...

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Bibliographic Details
Published in:Organic letters 2001-11, Vol.3 (23), p.3651-3653
Main Authors: Boeckman, Robert K, Reed, Jessica E, Ge, Ping
Format: Article
Language:English
Subjects:
Alkenes - chemistry
Aza Compounds - chemistry
Catalysis
Cyclization
Indicators and Reagents
Palladium
Pyrazoles - chemical synthesis
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Summary:A novel Pd(0)-catalyzed carbonylation of both isolable 1,2-diaza-1,3-butadienes and those generated in situ by extrusion of SO2 and CO2 from heterocyclic precursors is described. The reaction proceeds at room temperature to 110 °C under 1−2 atm of CO to afford 2,3-pyrazol-1(5H)-ones in good to excellent yields. The effect of catalyst structure and stability on the carbonylation reaction is evaluated.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol016565x