Abstract

An efficient synthesis of 1-aminoadamantane (amantadine) derivatives is described. This synthesis features acid-promoted aza-Prins cyclization of 7-methylenebicyclo[3.3.1]nonan-3-one oximes, which are readily prepared from 1,3-adamantanediol via a Grob fragmentation and the subsequent oximation, to give various 3-substituted 1-(alkoxyamino)adamantanes. After the reduction of alkoxyamines, not only 3-substituted 1-aminoadamantanes, but also chiral 2,5-disubstituted derivatives were obtained in good yields.

An efficient synthesis of 1-aminoadamantane (amantadine) derivatives is described. This synthesis features acid-promoted aza-Prins cyclization of 7-methylenebicyclo[3.3.1]nonan-3-one oximes, which are readily prepared from 1,3-adamantanediol via a Grob fragmentation and the subsequent oximation, to give various 3-substituted 1-(alkoxyamino)adamantanes. After the reduction of alkoxyamines, not only 3-substituted 1-aminoadamantanes, but also chiral 2,5-disubstituted derivatives were obtained in good yields.

中文翻译：

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通过7-亚甲基双环[3.3.1] nonan-3-one肟的Aza-Prins环化方便地进入1-氨基金刚烷衍生物

摘要

描述了1-氨基金刚烷（金刚烷胺）衍生物的有效合成。该合成的特征是7-亚甲基双环[3.3.1]壬南-3-酮肟的酸促进的氮杂-普林斯环化反应，这些反应很容易由1,3-金刚烷二醇经Grob裂解和随后的肟化反应制得，得到各种3-取代的1-（烷氧基氨基）金刚烷。在还原烷氧基胺之后，不仅以高收率获得了3-取代的1-氨基金刚烷，而且还获得了手性的2，5-二取代的衍生物。

描述了1-氨基金刚烷（金刚烷胺）衍生物的有效合成。该合成的特征是7-亚甲基双环[3.3.1]壬南-3-酮肟的酸促进的氮杂-普林斯环化反应，这些反应很容易由1,3-金刚烷二醇经Grob裂解和随后的肟化反应制得，得到各种3-取代的1-（烷氧基氨基）金刚烷。在还原烷氧基胺之后，不仅以高收率获得了3-取代的1-氨基金刚烷，而且还获得了手性的2，5-二取代的衍生物。