6533b7d8fe1ef96bd126999f
RESEARCH PRODUCT
Acid- and Base-Catalysis in the Mononuclear Rearrangement of Some (Z)-arylhydrazones of 5-Amino-3-benzoyl-1,2,4-oxadiazole in Toluene: Effect of Substituents on the Course of Reaction
Domenico SpinelliFranco GhelfiVincenzo FrennaSalvatore MarulloFrancesca D'annasubject
SubstituentOxadiazoleAlkaliesMedicinal chemistryCatalysisDioxanesStructure-Activity RelationshipAcid catalysischemistry.chemical_compoundPiperidinesUreaOrganic chemistryAminesTrichloroacetic AcidBenzeneBiological ProductsOxadiazolesMolecular StructureArylMRH acid- and base-catalysis kinetic measurementsOrganic ChemistryHydrazonesTemperatureWaterSettore CHIM/06 - Chimica OrganicaTolueneSolventKineticschemistryMononuclear rearrangements of heterocycles; (Z)-Arylhydrazones; acid catalysis; base catalysis.PiperidineHydrophobic and Hydrophilic InteractionsToluenedescription
The reaction rates for the rearrangement of eleven (Z)-arylhydrazones of 5-amino-3-benzoyl-1,2,4-oxadiazole 3a-k into the relevant (2-aryl-5-phenyl-2H-1, 2,3-triazol-4-yl)ureas 4a-k in the presence of trichloroacetic acid or of piperidine have been determined in toluene at 313.1 K. The results have been related to the effect of the aryl substituent by using Hammett and/or Ingold-Yukawa-Tsuno correlations and have been compared with those previously collected in a protic polar solvent (dioxane/water) as well as with those on the analogous rearrangement of the corresponding (Z)-arylhydrazones of 3-benzoyl-5-phenyl-1,2,4-oxadiazole 1a-k in benzene. Some light can thus be shed on the general differences of chemical reactivity between protic polar (or dipolar aprotic) and apolar solvents.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2011-01-01 |