Heteroadamantanes and their derivatives. 12. Synthesis of 1,3,6-triazahomoadamantane — A new heterocyclic system
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8-Nitro-1,3,6-triazahomoadamantane was obtained by the condensation of nitromethane with an equimolar mixture of 1,4,6,9-tetraazatricyclo[188.8.131.52.9]dodecane and hexamethylenetetramine. By reducing it with hydrazine hydrate in the presence of Raney nickel, 8-amino-1,3,6-triazahomoadamantane was synthesized. This was converted to 8-bromo-1,3,6-triazahomoadamantane by the action of sodium nitrite in hydrobromic acid. The 1,3,6-triazahomoadamantane was obtained by reduction of the bromo derivative with hydrazine hydrate in the presence of Raney nickel. The structures of the compounds synthesized were confirmed by PMR and mass spectroscopy.
KeywordsSodium Spectroscopy Nickel Mass Spectroscopy Hydrate
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