On the application of the extended Fujita–Nishioka equation to polysubstituted systems. A kinetic study of the rearrangement of several poly-substituted Z-arylhydrazones of 3-benzoyl-5-phenyl-1,2,4-oxadiazole into 2-aryl-4-benzoylamino-5-phenyl-1,2,3-triazoles in dioxane/water

Fluorinated Triazoles and Tetrazoles

“…Recently, a number of chiral phosphoramidite ligands 127 containing 1,2,3-triazole ring at the 3,3′-positions of the binol scaffold were synthesized by McErlean et al [ 112 ]. [ 114 ]. Haszeldine in 1970 developed several routes for the synthesis of perfl uorobenzofused 1,2,3-triazole 131 from decafl uoroazoxybenzene 132 , tetrafl uoro-ophenylenediamine 133 , and 2,3,4,5,6-pentafl uoronitrobenzene 134 [ 115 ].…”

On the use of multi-parameter free energy relationships: the rearrangement of (Z)-arylhydrazones of 5-amino-3-benzoyl-1,2,4-oxadiazole into (2-aryl-5-phenyl-2H-1,2,3-triazol-4-yl)ureas

“…11 Particular attention has been devoted to the study of the mononuclear rearrangement of heterocycles (MRH, as named by Boulton and Katritzky), 12 a reaction that plays a central role in the large field of ring-to-ring interconversion. 13 In this research line, we have inter alia measured the rearrangement rates 14 of several substituted (Z)-arylhydrazones of 3-benzoyl-5-phenyl-1,2,4-oxadiazole (1ae38a; see Scheme 1) into the relevant 2-aryl-4-benzoylamino-5-phenyl-1,2,3-triazole (1be38b) in dioxane/water (D/W; 1:1; v:v) in a wide range of pS þ (an operational scale of proton concentration in D/W).…”

“…14 Recently we have addressed our attention to the research of acidic catalysis in MRH processes: via a well-designed modification of the structure of the 1,2,4-oxadiazole ring (an amino group introduced at C-5 has strongly increased the basic character of N 4 ) 27 we have obtained (Z)-arylhydrazones able to rearrange 'also' via a specific-acid-catalyzed pathway.…”

“…29 Starting from the above results we have now synthesized five new ortho-substituted (X¼2-Me, 2-F, 2-Cl, 2-Br, and 2-NO 2 : 33c, 35ce38c) and ten new polysubstituted (di-, tri-, and foursubstituted: X 2 ¼2,3-Me 2 , 2,5-Me 2 , 3,4-Me 2 , 2,3-Cl 2 , 2,4-Cl 2 , 2,5-Cl 2 , 2,6-Cl 2 , 3,5-Cl 2 ; X 3 ¼2,4,6-Cl 3 ; X 4 ¼2,3,5,6-F 4 : 1c, 3c, 4c, 8ce11c, 13c, 16c, 17c) (Z)-arylhydrazones of 5-amino-3-benzoyl-1,2,4-oxadiazole and studied their MRH into the relevant (2-aryl-5-phenyl-2H-1,2,3-triazol-4-yl)ureas with the following aims:…”

“…(3) to ascertain if the kinetic steric acceleration observed in 2,6-dihalogeno (Z)-phenylhydrazones of 3-benzoyl-5-phenyl-1, 2,4-oxadiazole (11a, 16ae18a) 14 represents a general behavior in the MRH of (Z)-arylhydrazones of 3-benzoyl-1,2,4-oxadiazoles and in that case, looking if it also works in the acid-catalyzed pathway;…”