1,2,5-Oxadiazole (Furazan) Derivatives from Benzoylnitromethane and Dipolarophiles in the Presence of DABCO: Structure and Intermediates

1,2,5-Oxadiazole (Furazan) Derivatives from Benzoylnitromethane and Dipolarophiles in the Presence of DABCO: Structure and Intermediates

Furazan (1,2,5‐oxadiazole) derivatives are obtained along with isoxazolines from the reaction of benzoylnitromethane with dipolarophiles in the presence of DABCO. Furazans are shown to derive from the intermediate dibenzoylfuroxan (3,4‐dibenzoyl‐1,2,5‐oxadiazole‐5‐oxide) and dipolarophiles under hyd...

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Veröffentlicht in:European Journal of Organic Chemistry 2006-07, Vol.2006 (13), p.3016-3020
Hauptverfasser: Cecchi, Luca, De Sarlo, Francesco, Faggi, Cristina, Machetti, Fabrizio
Format: Artikel
Sprache:eng
Schlagworte:
Cycloaddition
DABCO
Heterocycles
Nitro compounds
Rearrangement
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Zusammenfassung:Furazan (1,2,5‐oxadiazole) derivatives are obtained along with isoxazolines from the reaction of benzoylnitromethane with dipolarophiles in the presence of DABCO. Furazans are shown to derive from the intermediate dibenzoylfuroxan (3,4‐dibenzoyl‐1,2,5‐oxadiazole‐5‐oxide) and dipolarophiles under hydrolytic conditions. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200600039