Ring-opening of 3-substituted azetidines as an entry to triazolodiazepines

This is the authors' abstract. We don't add key points for this paper.

Prochiral 3-substituted azetidines bearing a chiral N -substituent may undergo ring-opening reactions with electrophiles, such as benzyl or propargyl bromide, to generate diastereomeric products with moderate selectivity. In the case of the resulting 3-bromo- N -propargylamines, reaction with sodium azide followed by intramolecular azide-alkyne cycloaddition led to substituted tetrahydro triazolodiazepine derivatives. These findings expand the utility of azetidine scaffolds for the construction of more complex nitrogen-containing heterocycles. • Ring-opening of prochiral 3-substituted azetidines with electrophiles gave diastereomeric products with modest selectivity. • Both N - and C-3 substituents of azetidines were varied to study the diastereoselectivity of the ring-opening reaction. • 3-azido- N -propargylamines, produced from the 3-bromo precursors, gave triazolodiazepines by intramolecular cycloaddition.