Heteroaromatic Fused Derivatives of Tetracyclo4,11.05,9>undecane

Article abstract of DOI:10.1021/jo00004a029

A series of rigid syn-orthocyclophanes is prepared by the Friedlaender condensation of appropriate o-aminobenzaldehyde derivatives with tetracyclo<6.3.0.0^4,11.0^5,9>undecane-2,7-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 mechanics calculations agree closely with X-ray analysis in describing the structural properties of these cyclophanes.Analysis of the 1H-NMR and UV spectra as well as the reduction potentials of these molecules support a moderate electronic interaction between the decks.Initial investigations regarding their ability to serve as cleft-type hosts are described.