title: Synthesis of triazolo-fused benzoxazepines and benzoxazepinones via Passerini reactions followed by 1,3-dipolar cycloadditions.
abstract: Azidobenzaldehydes can be used in Passerini three-component condensations to synthesize small collections of triazolo-fused heterocycles in an efficient and combinatorial fashion upon post-condensation azide-alkyne cycloadditions. Triazolo-fused benzoxazepinones were obtained in moderate to good overall yields with a concise two-step protocol. Triazolo-fused benzoxazepines were instead prepared by means of a longer, yet straightforward route comprising a Passerini reaction, hydrolysis of the ester moiety, O-alkylation with propargylic bromides, and 1,3-dipolar cycloaddition.
authors.affiliation: Department of Chemistry and Industrial Chemistry, University of Genova, Via Dodecaneso 31, 16146 , Genoa, Italy.
authors.forename: Fabio
authors.initials: F
authors.lastname: De Moliner
authors.forename: Martina
authors.initials: M
authors.lastname: Bigatti
authors.forename: Chiara
authors.initials: C
authors.lastname: De Rosa
authors.forename: Luca
authors.initials: L
authors.lastname: Banfi
authors.forename: Renata
authors.initials: R
authors.lastname: Riva
authors.forename: Andrea
authors.initials: A
authors.lastname: Basso
mesh_terms: D000478:Alkylation; D048588:Benzoxazines / Q000138:chemical synthesis* / Q000737:chemistry*; D061565:Cycloaddition Reaction; D006868:Hydrolysis; D014230:Triazoles / Q000737:chemistry*
chemical_list: D048588:Benzoxazines; D014230:Triazoles