An alicyclic 1,5,9-triketone 2,6-bis[(2-oxocyclohexyl)methyl]cyclohexanone, its cyclic form and reactions with N-nucleophiles

The alicyclic 1,5,9-triketone 2,6-bis[(2-oxocyclohexyl)methyl]cyclohexanone, its cyclic form, and the product of its dehydration have been studied under Leuckart reaction conditions, with ammonium acetate in acetic acid and with hydroxylamine. The composition of the melt of the cyclic form has been determined. The obtained polycyclic products of N-heterocyclization confirm the existence of intermediate forms of the cyclization of 1,5,9-triketone in the reaction mixture. The structure and stereochemistry of the reaction products were determined using 1D selective COSY, NOE difference, and 2D NMR experiments (1H-1H COSY, HSQC, HMBC, and NOESY).