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Synthesis of Fused 3‑Aminoazepinones via Trapping of a New Class of Cyclic Seven-Membered Allenamides with Furan

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posted on 18.07.2014, 00:00 by Ben Schurgers, Ben Brigou, Zofia Urbanczyk-Lipkowska, Dirk Tourwé, Steven Ballet, Frank De Proft, Guy Van Lommen, Guido Verniest
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.