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)-phenyl-hydrazone 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.
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 / V., Frenna; A., Palumbo Piccionello; B., Cosimelli; Ghelfi, Franco; D., Spinelli. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1099-0690. - STAMPA. - /:(2014), pp. 7006-7014. [10.1002/ejoc.201402569]
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
GHELFI, Franco;
2014
Abstract
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)-phenyl-hydrazone 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.
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