CONVENIENT PREPARATION OF AROMATIC-ALDEHYDES VIA DDQ OXIDATION - APPLICATION IN THE SYNTHESIS OF A TRIPODAND CONTAINING OCTAHYDROACRIDINE MOIETIES

7-Methyloctahydroacridines 7a-d were obtained by a one-pot imine conde nsation/Lewis acid-catalyzed cyclization from aniline derivatives 5a-d and aldehyde 6. Only those compounds 7 could be oxidized with DDQ to the corresponding octahydroacridine-7-carbaldehydes 9, which bear a me ta-chloro or bromo substituent (with respect to the methyl group) in a ddition to the para-amino group (i.e. 7c,d --> 9c,d). Aldehyde 9c was further converted to the novel tripodand 11 which was characterized by X-ray crystal structure analysis.