Exploiting the CNC Side Chain in Heterocyclic Rearrangements: Synthesis of 4(5)-Acylamino-imidazoles.
- Authors: PALUMBO PICCIONELLO, A; BUSCEMI, S; VIVONA, N; PACE, A
- Publication year: 2010
- Type: Articolo in rivista (Articolo in rivista)
- Key words: oxadiazole, imidazole, heterocyclic rearrangement, transamination, heterogeneous catalysis
- OA Link: http://hdl.handle.net/10447/52096
Abstract
A new variation on the Boulton-Katritzky reaction is reported, namely, involving use of a CNC side chain. A novel Montmorillonite-K10 catalyzed nonreductive transamination of a 3-benzoyl-1,2,4-oxadiazole afforded a 3-(r-aminobenzyl)-1,2,4-oxadiazole, which was condensed with benzaldehydes to afford the corresponding imines. In the presence of strong base, these imines underwent Boulton-Katritzky-type rearrangement to afford novel 4(5)-acylaminoimidazoles.