The synthesis of the title compound (4b) has been completed: its rearrangement (in dioxane/water; 1:1, v/v) into N-(2,4-dinitrophenyl)-5-phenyl-2H-1,2,3-triazol-4-ylurea (7) has been quantitatively studied in a wide reactivity (at 293 K, kA 10-8 -4 s-1) and pS+ (4.5 - 14.1) range and compared with that of the Z-2,4-dinitrophenylhydrazone of 3-benzoyl-5-phenyl-1,2,4-oxadiazole (10), of the 3-(p-nitro)phenylureine of 5-phenyl-1,2,4-oxadiazole (13), and of N-(5-phenyl-1,2,4-oxadiazol-3-yl)-N′-p-nitrophenylformamidine (14). The results (reactivity, occurrence of specific or general base-catalysis, evidence for or absence of rate-limiting constants) have been well interpreted considering the structure of the side-chains involved and the stability of the final rings obtained in the rearrangements.
Cosimelli B., Guernelli S., Spinelli D., Buscemi A., Frenna V., Macaluso G. (2001). On the synthesis and reactivity of the Z-2,4-dinitrophenylhydrazone of 5-amino-3-benzoyl-1,2,4-oxadiazole. JOURNAL OF ORGANIC CHEMISTRY, 66(18), 6124-6129 [10.1021/jo0157270].
On the synthesis and reactivity of the Z-2,4-dinitrophenylhydrazone of 5-amino-3-benzoyl-1,2,4-oxadiazole
Guernelli S.;
2001
Abstract
The synthesis of the title compound (4b) has been completed: its rearrangement (in dioxane/water; 1:1, v/v) into N-(2,4-dinitrophenyl)-5-phenyl-2H-1,2,3-triazol-4-ylurea (7) has been quantitatively studied in a wide reactivity (at 293 K, kA 10-8 -4 s-1) and pS+ (4.5 - 14.1) range and compared with that of the Z-2,4-dinitrophenylhydrazone of 3-benzoyl-5-phenyl-1,2,4-oxadiazole (10), of the 3-(p-nitro)phenylureine of 5-phenyl-1,2,4-oxadiazole (13), and of N-(5-phenyl-1,2,4-oxadiazol-3-yl)-N′-p-nitrophenylformamidine (14). The results (reactivity, occurrence of specific or general base-catalysis, evidence for or absence of rate-limiting constants) have been well interpreted considering the structure of the side-chains involved and the stability of the final rings obtained in the rearrangements.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
