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

  • July 1, 2014

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.

 

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