1252578-07-6Relevant articles and documents
On the use of multi-parameter free energy relationships: The rearrangement of (Z)-arylhydrazones of 5-amino-3-benzoyl-1,2,4-oxadiazoleinto(2-aryl-5-phenyl- 2H-1,2,3-triazol-4-yl)ureas
D'Anna, Francesca,Frenna, Vincenzo,ZairaLanza, Camilla,MacAluso, Gabriella,Marullo, Salvatore,Spinelli, Domenico,Spisani, Raffaella,Petrillo, Giovanni
supporting information; experimental part, p. 5442 - 5450 (2010/08/13)
By using a multi-parameter approach (a combination of Hammett/Ingold- Yukawa-Tsuno/Fujita-Nishioka free energy relationships) the mononuclear rearrangements of heterocycles (MRH) rates for five new ortho-substituted and ten new di-, tri-, or tetra-substituted (Z)-arylhydrazones of 5-amino-3-benzoyl-1,2,4-oxadiazole into the relevant (2-aryl-5-phenyl-2H-1,2,3- triazol-4-yl)ureas (in dioxane/water and in a large range of pS+ values) have been related to the electronic and proximity effects exerted by the present substituents, also considering previous results on some mono meta-and para-substituted (Z)-arylhydrazones.In every case, excellent correlation coefficients have been calculated (r2 or R2>0.996).Once more the study of MRH has furnished an interesting panel of different reactivity (three pathways of reaction have been evidenced: general-base- catalyzed, uncatalyzed, and specific-acid-catalyzed) and this has been useful in enlightening how polysubstitution can differently affect the MRH rates.Moreover 2,6-disubstitution on the (Z)-arylhydrazono moiety causes a significant increase of the reactivity in all of the three studied pathways.All of the collected data appear useful for understanding structure-reactivity/activity relationships in polysubstituted compounds.
