氨基
化学
十一烷
氮气
反应条件
反应机理
立体化学
药物化学
计算化学
有机化学
催化作用
作者
Mikhail A. Kalinin,А. В. Медведько,Mikhail E. Minyaev,С. З. Вацадзе
标识
DOI:10.1021/acs.joc.3c00514
摘要
A new approach to the preparation of N,N'-unsymmetrically substituted 9-aminobispidines through aminal bridge removal reaction has been developed, the principal feature of which is the ability to selectively functionalize all three nitrogen atoms. The intermediates of 1,3-diazaadamantane's aminal bridge removal reaction are characterized, and the mechanism of this reaction is proposed based on the analysis of their structures. Representatives of the previously unknown saturated heterocyclic 1,5,9-triazatricyclo[5.3.1.03,8]undecane system were obtained and structurally characterized. Thus, it was possible for the first time to obtain 3,7,9-trisubstituted bispidines containing acetyl, Boc, and benzyl groups at nitrogen atoms, which can be independently removed (orthogonal protective groups).
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