Heteroadamantanes and their derivatives

Synthesis of 3,6-diazahomoadamantane

“…In the present communication we report on the synthesis of 3,6-diazahomoadamantane in a similar way. For this purpose, as initial ketone we used 1-phenylsulfanylpropan-2-one (I); its condensation with 1,3,6,8-tetraazatricyclo-[4.4.1.1 3,8 ]dodecane in propan-2-ol afforded more than 60% of 1-phenylsulfanyl-3,6-diazahomoadamantan-9-one (II) (Scheme 1). δ C 65.63 and 59.45 ppm from four bridging methylene carbon atoms.…”

“…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.By condensation of methyl ketones with 1,3,6,8-tetraazatricyclo[4.4.1.1 3,8 ]dodecane [1] and subsequent Wolff-Kishner reduction of the resulting 3,6-diazahomoadamantan-9-ones we obtained a number of 3,6-diazahomoadamantane derivatives substituted at the bridgehead position [2][3][4]. In the present communication we report on the synthesis of 3,6-diazahomoadamantane in a similar way.…”

Synthesis of 1-(pyridin-4-yl)-3,6-diazahomoadamantane and its derivatives

“…We synthesized 1-(pyridin-4-yl)-3,6-diazahomoadamantan-9-one (II) using 1-(pyridin-4-yl)propan-2-one (I) as initial methyl ketone; it was prepared by acylation of 4-methylpyridine with acetyl chloride according to the procedure described in [6]. The condensation of ketone I with 1,3,6,8-tetraazatricyclo[4.4.1.1 3,8 ]dodecane gave compound II in more than 40% yield (Scheme 1).…”

“…We previously [1] developed a procedure for the condensation of methyl ketones with 1,3,6,8-tetraazatricyclo[4.4.1.1 3,8 ]dodecane, which ensured synthesis of 3,6-diazahomoadamantane derivatives substituted at the bridgehead position [2][3][4][5]; Wolff-Kishner reduction of the latter gave a number of 3,6-diazahomoadamantane derivatives having aliphatic and aromatic substituents. No analogous compounds with heteroaromatic substituents were reported.…”