Reactions of 3-substituted 3-azabicyclo[3.3.1]nonan-9-ones with nitrogen-containing nucleophiles |
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Authors: | A I Moskalenko V I Boev |
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Institution: | (1) Lipetsk State Pedagogical University, ul. Lenina 42, Lipetsk, 398020, Russia |
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Abstract: | Condensation of 3-substituted 3-azabicyclo3.3.1]nonan-9-ones with hydroxylamine and hydrazine hydrate gave the corresponding oximes, hydrazones, and azines. Reductive amination of the title compounds in the presence of sodium triacetoxyhydridoborate led to the formation of 3-substituted 3-azabicyclo3.3.1]nonan-9-amines which were converted into the corresponding dihydrochlorides by treatment with dry hydrogen chloride. Treatment of 3-tert-butoxycarbonyl derivatives with HCl under analogous conditions was accompanied by elimination of the tert-butoxycarbonyl group to produce 3-azabicyclo3.3.1]nonan-9-amine dihydrochlorides. |
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