The condensation product of adamantan-1-amine with formaldehyde, 1,3,5-tri(1-adamantyl)-1,3,5-triazacyclohexane, was treated with three different types of ketones: symmetric (RCH 2 ) 2 CO, nonsymmetric RCH 2 COCH 3 , and acetone to obtain 1,5-R- N , N ′-di(1-adamantyl) bispidin-9-ones, N , N ′-di(1-adamantyl)-1-[(1-adamantylamino)methyl]-5-methylbispidin-9-one, and N , N ′-di(1-adamantyl)-1,5-bis[(1-adamantylamino)methyl]bispidin-9-one. 1,5-R- N , N ′-Di(1-adamantyl)bispidin-9-ones were reduced with sodium borohydride to 1,5-R- N , N ′-di(1-adamantyl)bispidin-9-ols.

A new type of 1,3-diazaadanamtan-6-ones was synthesized by heating the 3,7-di(tert-butyl)-1-[(tert-butylamino)methyl]bispidin-9-one derivatives with concentrated hydrobromic acid followed by condensation with formaldehyde.

A condensation of tetramethylenediethylenetetramine with 4-phenylbutan-2-one and its derivatives such as 4-(4-hydroxyphenyl)butan-2-one, 4-(4-methoxyphenyl)butan-2-one, and 4-(4-hydroxy-3-methoxyphenyl)butan-2-one led to fragrant compounds: 1-benzyl-3,6-diazahomoadamantan-9-one and its derivatives at the benzene ring.

5-Benzyl-1,3-diazaadamantan-6-one and its derivatives at the benzene ring were synthesized by the condensation of hexamethylenetetramine with 4-phenylbutan-2-one (jasmarol) and its derivatives, viz. , 4-(4-hydroxyphenyl)butan-2-one (raspberry ketone), 4-(4-methoxyphenyl)butan-2-one (anisylacetone), and 4-(4-hydroxy-3-methoxyphenyl)butan-2-one (vanillylacetone, zingerone).

Heating of 3,7-di( tert -butyl)-1,5-dimethyl-3,7-diazabicyclo[3.3.1]nonan-9-one with hydro-bromic acid gave 1,5-dimethyl-3,7-diazabicyclo[3.3.1]nonan-9-one (1,5-dimethylbispidin-9-one). Condensation of this compound or 1,5-dimethylbispidin-9-ol with dialdehydes afforded new compounds containing two 1,3-diazaadamantane moieties in one molecule, which are connected either directly or through spacers.

By condensation of 4-phenylbutan-2-one with tetramethylenediethylenetetramine 1-benzyl-3,6-diazahomoadamantan-9-one was synthesized. Further nitration of 1-benzyl-3,6-diazahomoadamantan-9-one yielded 1-(4-nitrobenzyl)-3,6-diaɛahomoadamantan-9-one. The modification of the nitro and carbonyl groups resulted in the formation of 1-benzyl-3,6-diazahomoadamantane and its derivatives with functional groups in the benzene ring and at the bridge carbon atom C 9 .

Condensation of 1,3,5-tri(tert-butyl)-1,3,5-triazacyclohexane with acetone gave 3,7-di(tert-butyl)-1,5-bis[(tert-butylamino)methyl]bispidin-9-one. Reactions with ethyl methyl ketone and other ketones of the formula RCH2COCH3 yielded 5-R-3,7-di(tert-butyl)-1-[(tert-butylamino)methyl]bispidin-9-ones, while reactions with diethyl ketone and other symmetrical ketones of the formula RCH2COCH2R afforded 1,5-R-3,7-di(tert-butyl)bispidin-9-ones.

Condensation of 1-phenylsulfanylpropan-2-one with 1,3,6,8-tetraazatricyclo[4.4.1.1 3,8 ]dodecane gave 1-phenylsulfanyl-3,6-diazahomoadamantan-9-one which was reduced to 1-phenylsulfanyl-3,6-diazahomoadamantane, and the latter was subjected to desulfurization over Raney nickel to obtain previously unknown 3,6-diazahomoadamantane. Heating of 9-phenyl-3,6-diazahomoadamantan-9-ols with Raney nickel resulted in reduction of the hydroxy group with formation of 9-phenyl-3,6-diazahomoadamantanes.