A synthesis of 6-azabicyclo[3.2.1]octanes. The role of N-substitution.
A synthesis of 6-azabicyclo[3.2.1]octanes. The role of N-substitution.
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DOI：
10.1021/jo702444c
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发表时间：
2008-01
期刊：
影响因子：
--
通讯作者：
Aravinda B. Pulipaka;S. Bergmeier
中科院分区：
文献类型：
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作者：
Aravinda B. Pulipaka;S. Bergmeier
叠氮嘧啶与亲核试剂的分子内环化反应是生成杂环和碳环体系的有效途径。我们对利用这种环化反应合成6-氮杂环[3.2.1]辛烷特别感兴趣。我们在这里报道了一种新的合成方法的发展，这种合成方法是氮化吡啶-亲核试剂环化所必需的。我们还报道了在氮氮上用三种不同取代的叠氮环化。我们发现，n -二苯基膦酰和N-H叠氮吡啶虽然参与了初始开环反应，但并没有得到期望的双环体系。相比之下，氮氮上的一个鼻基可以有效地形成双环系统，并且可以很容易地去保护。
The intramolecular cyclization reactions of aziridines with pi-nucleophiles can be a useful route to a number of heterocyclic and carbocyclic ring systems. We were particularly interested in the use of this cyclization reaction for the synthesis of 6-azabicyclo[3.2.1]octanes. We report here the development of a new synthesis of the aziridine necessary for the aziridine--pi-nucleophile cyclization. We also report on the cyclization of aziridines with three different substitutions on the aziridine nitrogen. We have found that N-diphenylphospinyl and N-H aziridines, while participating in the initial ring-opening reaction, do not lead to the desired bicyclic ring systems. In contrast, a nosyl group on the aziridine nitrogen leads efficiently to the bicyclic ring system and can be readily deprotected.