Synthetic pathways for substituted decahydroacrydine-1,8-diones in the reaction of amination of methylene-(arylidene-, 5-R-2-furfurylidene)-bis-cyclohexane-1,3-diones and by means of condensation of cyclic enaminoketones with aldehydes of various classes were found. Peculiarities of oxymation and reduction of decahydroacrydine-1,8- diones related to the nature of the C9 substituent in the heteroring were revealed. With the aid of Fischer reaction, hexahydrobisindolo[2,3-a:3',2'-j] acrydines were obtained for the first time. The structures of the compounds synthesized were deduced from chromato-mass-spectrometric, 1H and 13C NMR data.