Synthesis of Amino-1,2,4-triazoles by Reductive ANRORC Rearrangements of 1,2,4-Oxadiazoles.
- Autori: PALUMBO PICCIONELLO, A; GUARCELLO, A; BUSCEMI, S; VIVONA, N; PACE, A
- Anno di pubblicazione: 2010
- Tipologia: Articolo in rivista (Articolo in rivista)
- Parole Chiave: oxadiazole, triazole, heterocycles rearrangement
- OA Link: http://hdl.handle.net/10447/52092
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.