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Unexpected Substituent Effects in the Iso-Heterocyclic Boulton-Katritzky Rearrangement of 3-Aroylamino-5-Methyl-1,2,4-Oxadiazoles: a Mechanistic Study

  • Authors: Frenna, Vincenzo; Lo Meo, Paolo; Palumbo Piccionello, Antonio; Spinelli, Domenico
  • Publication year: 2019
  • Type: Articolo in rivista
  • OA Link:


The kinetics of the iso-heterocyclic mononuclear rearrangement of some 3-aroylamino-5-methyl-1,2,4-ozadiazoles was carefully examined under largely variable acidic or alkaline conditions. This reaction may proceed via two different mechanistic pathways (an uncatalyzed and a base-catalyzed one), as accounted for also by evaluation of the relevant activation parameters. Substituent effects, as quantified by means of Hammett's equation, appear relatively modest; however, they reveal some interesting anomalies, which enabled us to draw a very precise picture of the intimate reaction course.