title: Synthesis of fused 3-aminoazepinones via trapping of a new class of cyclic seven-membered allenamides with furan.
abstract: Novel tricyclic tetrahydroazepinones were synthesized via an in situ Diels-Alder reaction of furan with cyclic allenamides. These reactive intermediates are the first examples of cyclic seven-membered allenamides and were prepared starting from N-(2-chloroallyl)-2-allylglycine derivatives via ring-closing metathesis followed by dehydrochlorination. The trapping of the intermediate cycloallene with furan occurred endo- and regioselectively and provided a convenient entry into new building blocks for medicinal chemistry. The diastereoselectivity of the cycloaddition was confirmed using quantum chemical computations.
authors.affiliation: Research Group of Organic Chemistry, Department of Chemistry and Department of Bio-engineering Sciences, Faculty of Science and Bio-engineering Sciences and ‡Department of General Chemistry, Vrije Universiteit Brussel , Pleinlaan 2, B-1050 Brussels, Belgium.
authors.forename: Ben
authors.initials: B
authors.lastname: Schurgers
authors.forename: Ben
authors.initials: B
authors.lastname: Brigou
authors.forename: Zofia
authors.initials: Z
authors.lastname: Urbanczyk-Lipkowska
authors.forename: Dirk
authors.initials: D
authors.lastname: Tourwé
authors.forename: Steven
authors.initials: S
authors.lastname: Ballet
authors.forename: Frank
authors.initials: F
authors.lastname: De Proft
authors.forename: Guy
authors.initials: G
authors.lastname: Van Lommen
authors.forename: Guido
authors.initials: G
authors.lastname: Verniest