In the interaction of a series of 1-aryl-3-R-3-(2′-oxo-cycloalkyl)-1-propanones with o-aminophenol and o-phenylenediamine, depending on the structure of the reacting compounds, derivatives of 1,9a-tetra(tri)-methylene-9-oxa(aza)-4a-aza-1,2,4a,9a-tet-rahydrofluorene are formed. The interaction of 1-(o-hydroxyphenyl)- and 1-(o-aminophenyl)-3-R-3-(2′-oxocycloalkyl)-1-propanones with o-aminophenol, o-phenylenediamine, ethanolamine, and ethylenediamine leads to the formation of new heterocyclic systems: 2,7-dioxa-5-azatricyclo [4.3.3.01,5]dodecane, 7-oxa-2,5-diazatricyclo [4.3. 3.01,5]dodecane, and 2,5,7-triazatricyclo [4.3.3.01,5]dodecane.