Abstract
New cyclopentene-fused octahydropyridoquinolines and octahydrophenanthrolines were
prepared by a stereoselective three-component cyclocondensation of benzene-1,4-diamine,
cyclopenta-1,3-diene, and an aromatic aldehyde. Single-crystal X-ray diffraction data
provided evidence for the formation of cyclopentene-fused octahydropyridoquinolines
and octahydrophenanthrolines with a syn-planar arrangement of the cyclopentene rings. The cyclocondensation of benzene-1,4-diamine,
cyclopenta-1,3-diene, and formaldehyde gave new type of polycyclic compound containing
four cyclopentene moieties oriented in a mutually antiplanar manner.
Key words
Diels–Alder reactions - electrophilic aromatic substitutions - heterocycles - polycycles
- fused-ring systems
