Intramolecular electrophilic aromatic substitution reactions of 2-amidoacroleins: a new method for the preparation of tetrahydroisoquinolines, tetrahydro-3-benzazepines, and hexahydro-3-benzazocines |
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| Authors: | Fuchs J R Funk R L |
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| Institution: | Department of Chemistry, Pennsylvania State University, University Park, Pennsylvania 16802, USA. |
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| Abstract: | reaction: see text]. A variety of heterocyclic ring systems can be prepared by subjecting N-aryl-substituted 5-amido-1,3-dioxins to Lewis acids. The reactions proceed via catalyzed retrocycloadditions to afford 2-amidoacroleins and concomitant regioselective electrophilic aromatic substitution reactions. The transformation is also successful using dioxins with amides that are within the incipient ring to afford the analogous lactams. |
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