The reaction of various 1,2,4-oxadiazoles with an excess of hydrazine in DMF has been investigated. 3-Amino- 1,2,4-triazoles are produced through a reductive ANRORC pathway consisting of the addition of hydrazine to the 1,2,4-oxadiazole followed by ring-opening, ring-closure, and final reduction of the 3-hydroxylamino-1,2,4-triazole intermediate. The general applicability of 1,2,4-oxadiazoles ANRORC reactivity is demonstrated also in the absence of C(5)-linked electron-withdrawing groups.
PALUMBO PICCIONELLO, A., GUARCELLO, A., BUSCEMI, S., VIVONA, N., PACE, A. (2010). Synthesis of Amino-1,2,4-triazoles by Reductive ANRORC Rearrangements of 1,2,4-Oxadiazoles. JOURNAL OF ORGANIC CHEMISTRY, 75, 8724 [10.1021/jo102049r].
Synthesis of Amino-1,2,4-triazoles by Reductive ANRORC Rearrangements of 1,2,4-Oxadiazoles.
PALUMBO PICCIONELLO, Antonio;GUARCELLO, Annalisa;BUSCEMI, Silvestre;VIVONA, Nicolo';PACE, Andrea
2010-01-01
Abstract
The reaction of various 1,2,4-oxadiazoles with an excess of hydrazine in DMF has been investigated. 3-Amino- 1,2,4-triazoles are produced through a reductive ANRORC pathway consisting of the addition of hydrazine to the 1,2,4-oxadiazole followed by ring-opening, ring-closure, and final reduction of the 3-hydroxylamino-1,2,4-triazole intermediate. The general applicability of 1,2,4-oxadiazoles ANRORC reactivity is demonstrated also in the absence of C(5)-linked electron-withdrawing groups.
| File | Dimensione | Formato | |
|---|---|---|---|
|
jo102049r[1].pdf
Solo gestori archvio
Dimensione
729.73 kB
Formato
Adobe PDF
|
729.73 kB | Adobe PDF | Visualizza/Apri Richiedi una copia |
I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
