Synthesis and C.d. spectra of 6,6a,7,11b-tetrahydro-5H-indeno[2,1-c]-isoquinoline derivatives

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Abstract
We have synthesized the title compounds having two pharmacophores of the β-phenethylamine moiety with a semi-rigid spatial arrangement. They are very suitable for studies on the limit of the effect of electron exchange between two aromatic chromophores. X-Ray crystallography was carried out to determine the molecular structure of the skeleton compounds: 6,6a,7,11b-tetrahydro-5H-indeno[2,1-c]isoquinoline and 5,6,6a,7,8,12a-hexahydrobenz[a]phenanthridine. For compounds which showed positive Cotton effects, independent of the substituent pattern of the methoxy groups, in the region of the 1Lb benzenoid transition and the longer wavelength part of the 1B benzenoid transition, absolute configurations were determined by chemical correlation to (1R,2R)-(–)-2-aminoindan-1-ol and (1R,2R)-(–)-2-amino-5-methoxyindan-1-ol. The absolute configuration of the last-named was determined by X-ray crystrallography. An empirical rule was applied to determine the absolute configuration of the other compounds and was supported by, theoretical calculations.

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