Synthesis of Tricyclic Lactams from Heterocyclic Imines

Abstract

Starting from different heterocyclic imines, a large number of annulated tricyclic lactams were prepared in a two-step synthesis. First, methoxyamides with a phenyl ring in α- or β-position were generated. Finally, these substrates were converted to valero- and caprolactams, respectively, via intramolecular Friedel–Crafts cyclization in the presence of a Lewis acid. Additionally, effects of substituent groups at the phenyl ring in the electrophilic aromatic substitution were investigated.

Key words

heterocycles - imines - amides - lactams - cyclization - electrophilic aromatic substitution

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