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 Piccionello, Vincenzo Frenna, Barbara Cosimelli, Franco Ghelfi, Domenico Spinelli

Risultato della ricerca: Article

12 Citazioni (Scopus)

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. © 2014 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
Lingua originaleEnglish
pagine (da-a)7006-7014
Numero di pagine9
RivistaEuropean Journal of Organic Chemistry
Volume2014
Stato di pubblicazionePublished - 2014

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All Science Journal Classification (ASJC) codes

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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