6533b872fe1ef96bd12d2c77
RESEARCH PRODUCT
The Boulton-Katritzky Reaction: A Kinetic Study of the Effect of 5-Nitrogen Substituents on the Rearrangement of Some (Z)-Phenylhydrazones of 3-Benzoyl-1,2,4-oxadiazoles
Antonio Palumbo-piccionelloVincenzo FrennaFranco GhelfiBarbara CosimelliDomenico Spinellisubject
chemistryStereochemistryOrganic ChemistryKineticschemistry.chemical_elementPhysical and Theoretical ChemistryKinetic energyMedicinal chemistryIsomerizationNitrogendescription
The kinetics of the ring-into-ring conversion of some new (Z)-phenylhydrazones of 3-benzoyl-1,2,4-oxadiazole containing different nitrogen-substituents at C-5 (3b–d; X = NHMe, NMe2, and NHCOMe) into the relevant triazoles 4b–d have been examined in a wide range of pS+ (0.1–11.9) in 1:1 (v/v) dioxane/water solution. The obtained results have been compared with previous data concerning the (Z)-phenylhydrazone of 5-amino-3-benzoyl-1,2,4-oxadiazole (3a; X = NH2). All of the studied (Z)-phenylhydrazones rearrange through three different pathways (specific acid-catalysed, uncatalysed and general base-catalysed). The different effects of the substituents on the course of the rearrangement in the three pathways have been examined.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2014-09-24 | European Journal of Organic Chemistry |