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

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 ¹L_b 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.