Article Dans Une Revue Tetrahedron Letters Année : 2026

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

Résumé

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.

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hal-05507181 , version 1 (18-02-2026)

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Melvin Raulin, Bruno Drouillat, Jérome Marrot, François Couty, Karen Wright. Ring-opening of 3-substituted azetidines as an entry to triazolodiazepines. Tetrahedron Letters, 2026, 177, pp.155975. ⟨10.1016/j.tetlet.2026.155975⟩. ⟨hal-05507181⟩
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