Mononuclear rearrangements of heterocycles in water/β-CD: information on the real site of reaction from structural modifications of substrates and from proton concentration dependence of the reactivity

The effect of β-cyclodextrin (β-CD) on the reactivity in the base-catalyzed pathway for the rearrangement in water of some (Z)-hydrazones of 3-benzoyl-1,2,4-oxadiazoles (1b-f) into the relevant triazoles (2b-f) was investigated, finding different behavior as a function of the proton concentration. ESIMS and 1H NMR data evidence the formation of host-guest complexes. The whole of the experimental and calculated (MM2) data enabled us to draw some intriguing conclusions concerning the influence of the structures of the substrates and the nature of the formed host-guest complexes on the real site of the reaction.

Graphical abstractDownload full-size image