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. © 2014 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
|Numero di pagine||9|
|Rivista||European Journal of Organic Chemistry|
|Stato di pubblicazione||Published - 2014|
All Science Journal Classification (ASJC) codes
- Physical and Theoretical Chemistry
- Organic Chemistry
Palumbo Piccionello, A., Frenna, V., Cosimelli, B., Ghelfi, F., & Spinelli, D. (2014). 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. European Journal of Organic Chemistry, 2014, 7006-7014.