1451076-20-2Relevant academic research and scientific papers
Aza-heterocyclic frameworks through intramolecular π-system trapping of spiro-N-acyliminiums generated from isoindolinone
Chortani, Sarra,Othman, Mohamed,Lawson, Ata Martin,Romdhane, Anis,Ben Jannet, Hichem,Knorr, Michael,Brieger, Lukas,Strohmann, Carsten,Da?ch, Adam
supporting information, p. 2393 - 2403 (2021/02/16)
Spiro-acetoxylactams as key substrates were obtained straightforwardly by the tandem regioselective reduction/O-acylation of spiro-isoindolinone-imides. The latter were produced in large scale in three steps from homophthalic acid. These imides were useful to provide in one step isoindolinones bearing hydroxymethyl-amide functions, tethered at quaternary carbon centre with promising biological issues. Submitted to Br?nsted (TFA neat) and Lewis acid (trimethylsilyltrifluoro-methanesulfonic (TMSOTf) 10 mol%), the spiro-acetoxylactams undergo π-cyclization of spiro-N-acyliminiums to provide diastereoselectively with π-aromatic original pyrrolopyrido- and pyrroloazepino-isoindoles fused or not to aromatic systems. With π-olefins, pyrrolopyridines and pyrrolo-azepines fused to isoindoline or containing amino-acids were isolated. A reaction mechanism producing all these systems is also discussed.
Combining α-amidoalkylation reactions of N-acyliminium ions with ring-closing metathesis: Access to versatile novel isoindolones spirocyclic compounds
Pesquet, Anthony,Othman, Mohamed
supporting information, p. 5227 - 5231 (2013/09/02)
A novel approach to diversely spirocyclic isoindoles has been developed by using N-acyliminium/ring-closing metathesis strategy. Spirocyclization precursors, diolefinic, and enyne spiro-fused-isoindole derivatives have been obtained by a regioselective reduction of the spiro-imide compounds, followed by the allylation of the N-acyliminium intermediates (generated from the acetoxylactam compounds). Ruthenium catalyzed ring-closing metathesis of the above unsaturated derivatives provided novel spiroisoindoles.
