74675-59-5

Upstream product

• 59785-50-1 (E)-3-benzoyl-5-pgenyl-1,2,4-oxadiazole phenylhydrazone 
• 23572-06-7 phenyl(5-phenyl-1,2,4-oxadiazol-3-yl)methanone 
• 100-63-0 phenylhydrazine 
• 59785-50-1 (Z)-phenylhydrazone 3-benzoyl-5-phenyl-1,2,4-oxadiazole 

Downstream Products

• 96799-22-3 Acetic acid phenyl-phenylazo-(5-phenyl-[1,2,4]oxadiazol-3-yl)-methyl ester 
• 61308-15-4 2,5-diphenyl-4-benzoylamino-1,2,3-triazole 
• 59785-50-1 (Z)-phenylhydrazone 3-benzoyl-5-phenyl-1,2,4-oxadiazole 
• 59785-50-1 (E)-3-benzoyl-5-pgenyl-1,2,4-oxadiazole phenylhydrazone 
• 96798-87-7 1-Phenyl-3-(5-phenyl-1,2,4-oxadiazol-3-yl)indazole 

Relevant academic research and scientific papers

Mononuclear rearrangement of heterocycles in ionic liquids catalyzed by copper(II) salts

The reactivity of E- and Z-phenylhydrazones of 3-benzoyl-5-phenyl-1,2,4-oxadiazole in the presence of CuCl2 and Cu(ClO4)2·6H2O has been studied in four imidazolium ionic liquids [bmim][X] (X=BF4-, PF6-, SbF6- and CF3SO3-). The reaction may follow different mechanistic patterns, depending on the nature of the ionic liquid anion, accounting for both qualitative and kinetic data. In the presence of CuCl2, two processes take place at the same time, i.e., the E?Z isomerization and the rearrangement of Z-isomer into the relevant 4-benzoylamino-2,5-diphenyl-1,2,3-triazole. In contrast, in the presence of Cu(ClO4)2·6H2O, the rearrangement occurs only in solution of [bmim][BF4] and [bmim][CF3SO3]. Collected data show that the effect of the ionic liquid on the isomerization and the rearrangement is different. In particular, a higher cross-linking degree seems to favour the triazole, but disfavour the E?Z isomerization.

Isomerization and rearrangement of (E)- and (Z)-phenylhydrazones of 3-benzoyl-5-phenyl-1,2,4-oxadiazole: Evidence for a 'new' type of acid-catalysis by copper(II) salts in mononuclear rearrangement of heterocycles

A kinetic investigation in methanol of the title reaction has evidenced the occurrence of two processes: the 1 -E ? 1-Z isomerization and the rearrangement of the (Z)-isomer into the relevant 4-benzoylamino-2,5-diphenyl-1, 2,3-triazole (1-Z →T). The latter reaction is in line with the ability of the (Z)-phenylhydrazones of 3-benzoyl-1,2,4-oxadiazoles to undergo the so called mononuclear rearrangement of heterocycles (MRH). The occurrence of both the examined reactions is dependent on a Lewis-acid-catalysis. The obtained results have shown the possibility of a 'new' type of acid-catalysis (bifunctional catalysis by Lewis salts) in the MRH. This catalysis operates through a completely different mechanism with respect to the one recently observed, and deeply investigated, in the presence of protic acids for the (Z)-phenylhydrazone of 5-amino-3-benzoyl-1,2,4-oxadiazole, in both dioxane/water and toluene, for which the catalytic process was dependent on the protonation of N(4) ring-nitrogen of the 1,2,4-oxadiazole. As a matter of fact, the copper salts seem able to interact with the >C=N - NH - C6H5 moiety, yielding adducts which, in some cases, are prone to both isomerize and rearrange. Therefore, a similar behaviour in some manner parallel to that already observed in benzene in the presence of aliphatic amines (base-catalysis) has been evidenced. Copyright

A Kinetic Study on the Base-catalysed E --> Z Isomerization of Some Arylhydrazones of 3-Benzoyl-5-phenyl-1,2,4-oxadiazole: Effect of the Substituents in the Arylhydrazone Moiety

The kinetic data obtained in the study of the title reaction reveal unusual substituent effects.A logarithmic plot of reactivity data versus substituent constant (? and/or ?-) shows a 'zigzag' trend; it is suggested that this depends on a chang

Mononuclear Heterocyclic Rearrangements 5 (1). Kinetic Investigation of the Behaviour of (E)- and (Z)-Phenylhydrazones of 3-Benzoyl-5-phenyl-1,2,4-oxadiazole in Benzene. Isomerization and Rearrangement

The kinetic behaviour of the geometrical isomers I-E and I-Z of the title compound in the presence of piperidine in benzene has been investigated.The kinetic results suggest that I-Z rearranges directly into 2,5-diphenyl-4-benzoylamino-1,2,3-triazole (II)

Mononuclear Heterocyclic Rearrangement. Part 4 (1). Synthesis and Characterization of the E-isomer Phenylhydrazone of 3-Benzoyl-5-phenyl-1,2,4-oxadiazole

3-Benzoyl-5-phenyl-1,2,4-oxadiazole (I) with phenylhydrazine in acetic acid gives the two geometrical isomers, phenylhydrazones II-Z and II-E, which have been characterized by uv-visible, ir, and nmr spectra.The possible II-E II-Z isomerization as wel