A series of rigid syn-orthocyclophanes is prepared by the Friedlander condensation of appropriate o-aminobenzaldehyde derivatives with tetracyclo [6.3. 0.0'~ 11.~~] undecane-Z, 7-dione. The reaction may proceed in a stepwise fashion so that unsymmetrical layered compounds can be prepared. These species can be further elaborated by oxidation to quinolinequinones or N-oxides and quaternization to quinolinium salts. Molecular ...