6533b860fe1ef96bd12c37b3

RESEARCH PRODUCT

Heterocyclic rearrangements.N,N-diphenylhydrazones, oximes andO-methyloximes of 3-benzoyl-5-phenyl-1,2,4-oxadiazole

Nicolò VivonaSilvestre BuscemiMichele RucciaVincenzo Frenna

subject

chemistry.chemical_classificationchemistry.chemical_compoundIndazoleSemicarbazideBicyclic moleculeChemistryOrganic ChemistryOrganic chemistryOxadiazoleHydrazoneBenzeneMedicinal chemistry

description

The behaviour of (E)- and (Z)-N,N-diphenylhydrazones and O-Methyloximes of 3-benzoyl-5-phenyl-1,2,4-oxadiazole has been studied. When refluxed in benzene, or in dioxane-water (1:1), the (Z)-N,N-diphenylhydrazone 8Z gave the indazole 11 or the substituted semicarbazide 12, respectively. The O-methyloxime 14Z did not give any rearrangement. A criticism of the oximation reaction of 3-benzoyl-5-phenyl-1,2,4-oxadiazole is also reported.

https://doi.org/10.1002/jhet.5570220125