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RESEARCH PRODUCT
Synthesis of Amino-1,2,4-triazoles by Reductive ANRORC Rearrangements of 1,2,4-Oxadiazoles
Silvestre BuscemiAndrea PaceAntonio Palumbo-piccionelloAnnalisa GuarcelloNicolò Vivonasubject
oxadiazole triazole heterocycles rearrangementchemistry.chemical_classificationOrganic ChemistryHydrazineSettore CHIM/06 - Chimica OrganicaElectron acceptorMedicinal chemistryChemical synthesischemistry.chemical_compoundHydroxylaminechemistryChemical reductionAmine gas treatingReactivity (chemistry)description
The reaction of various 1,2,4-oxadiazoles with an excess of hydrazine in DMF has been investigated. 3-Amino- 1,2,4-triazoles are produced through a reductive ANRORC pathway consisting of the addition of hydrazine to the 1,2,4-oxadiazole followed by ring-opening, ring-closure, and final reduction of the 3-hydroxylamino-1,2,4-triazole intermediate. The general applicability of 1,2,4-oxadiazoles ANRORC reactivity is demonstrated also in the absence of C(5)-linked electron-withdrawing groups.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2010-11-18 | The Journal of Organic Chemistry |