36271-36-0Relevant academic research and scientific papers
Kinetic versus thermodynamic access to imidazoisoindolones, benzimidazoisoindolones, and [1,4]diazepinoisoindolones: Intramolecular nitrogen and π-aromatic trapping of N-acyliminium cation
Cul, Armelle,Da?ch, Adam,Decroix, Bernard,Sanz, Gérard,Van Hijfte, Luc
, p. 11029 - 11039 (2007/10/03)
Efficient assembly of substituted imidazo[2,1-a]isoindolones I is reported from suitable α,β-diamine IV (or corresponding β-nitroamine) and phthalic anhydride (1) in a three- or four-step sequence in good yields. The key step of this methodology is based on an intramolecular α-aza- amidoalkylation of the N-acyliminium species. Furthermore, when R2 is an aromatic moiety a competing α-amidoalkylation took place and imidazo[2,1-a]isoindolones (or benzimidazo[2,1-a]isoindolones) I and/or isoindolo[1,4]benzodiazepines III were obtained under kinetic or thermodynamic control. The chemoselectivity of these transformations is also discussed.
