10.1021/ol1013087.s001
Antonio Palumbo Piccionello
Antonio Palumbo
Piccionello
Silvestre Buscemi
Silvestre
Buscemi
Nicolò Vivona
Nicolò
Vivona
Andrea Pace
Andrea
Pace
Exploiting the CNC Side Chain in Heterocyclic Rearrangements: Synthesis of 4(5)-Acylamino-imidazoles
American Chemical Society
2010
presence
acylaminoimidazole
nonreductive transamination
imine
aminobenzyl
benzaldehyde
Boulton
Synthesi
Exploiting
variation
CNC Side Chain
benzoyl
CNC side chain
Heterocyclic Rearrangements
rearrangement
2010-08-06 00:00:00
Journal contribution
https://acs.figshare.com/articles/journal_contribution/Exploiting_the_CNC_Side_Chain_in_Heterocyclic_Rearrangements_Synthesis_of_4_5_Acylamino_imidazoles/2745280
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-(α-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.