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.

Frenna, V., Palumbo Piccionello, A., 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 [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

FRENNA, Vincenzo;PALUMBO PICCIONELLO, Antonio;
2014-01-01

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.
2014
Settore CHIM/06 - Chimica Organica
Frenna, V., Palumbo Piccionello, A., 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 [10.1002/ejoc.201402569].
File in questo prodotto:
File Dimensione Formato  
Frenna_et_al-2014-European_Journal_of_Organic_Chemistry.pdf

Solo gestori archvio

Descrizione: pdf
Dimensione 790.93 kB
Formato Adobe PDF
790.93 kB Adobe PDF   Visualizza/Apri   Richiedi una copia

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/10447/101892
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 17
  • ???jsp.display-item.citation.isi??? 16
social impact