Exploiting the CNC side chain in heterocyclic rearrangements: synthesis of 4(5)-acylamino-imidazoles.
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-(alpha-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.
Piccionello
Antonio Palumbo
AP
Dipartimento di Chimica Organica E. Paternò, Università degli Studi di Palermo, Viale delle Scienze-Parco d'Orleans II, I-90128 Palermo, Italy. apalumbo@unipa.it
Buscemi
Silvestre
S
Vivona
Nicolò
N
Pace
Andrea
A