A practical synthesis of (1S,4S)-2,5-diazabicyclo[2.2.1]heptane

被引：7
作者：
Beinat, Corinne [1 ]
Banister, Samuel D. [1 ,2 ]
McErlean, Christopher S. P. [1 ]
Kassiou, Michael [1 ,2 ,3 ]
机构：
[1] Univ Sydney, Sch Chem, Sydney, NSW 2006, Australia
[2] Brain & Mind Res Inst, Sydney, NSW 2050, Australia
[3] Univ Sydney, Discipline Med Radiat Sci, Sydney, NSW 2006, Australia
来源：
TETRAHEDRON LETTERS | 2013年 / 54卷 / 39期
关键词：
2,5-Diazabicyclo[2.2.1]heptane; Amines; Transannular cyclisation; Heterocycles; Nicotinic acetylcholine receptors; NICOTINIC ACETYLCHOLINE-RECEPTOR; LIGANDS; SCHIZOPHRENIA; DANOFLOXACIN;
D O I：
10.1016/j.tetlet.2013.07.092
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The rigid piperazine homologue 2.5-diazabicyclo[2.2.1]heptane (DBH) finds extensive application in medicinal chemistry and pharmaceutical research, but access to this scaffold is non-trivial. This letter details a concise synthetic sequence that gives ready access to DBH on gram scale. The route features a Staudinger reduction of an azide to facilitate a transannular cyclisation. (C) 2013 Elsevier Ltd. All rights reserved.
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收藏
页码：5345 / 5347
页数：3
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