Intramolecular electrophilic aromatic substitution reactions of 2-amidoacroleins: a new method for the preparation of tetrahydroisoquinolines, tetrahydro-3-benzazepines, and hexahydro-3-benzazocines.
[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.
Fuchs
J R
JR
Department of Chemistry, Pennsylvania State University, University Park, Pennsylvania 16802, USA.
Funk
R L
RL
D000171:Acrolein / Q000031:analogs & derivatives* / Q000737:chemistry; D001392:Azocines / Q000138:chemical synthesis*; D001552:Benzazepines / Q000138:chemical synthesis*; D007546:Isoquinolines / Q000138:chemical synthesis*; D009022:Morphine Derivatives / Q000138:chemical synthesis; D044005:Tetrahydroisoquinolines
D001392:Azocines; D001552:Benzazepines; D007546:Isoquinolines; D009022:Morphine Derivatives; D044005:Tetrahydroisoquinolines; C014843:1,2,3,4-tetrahydroisoquinoline; D000171:Acrolein