Synthesis of 3-Azabicyclo[3.2.0]heptane Derivatives as γ-Aminobutyric Acid Analogues through Intermolecular [2+2] Photocycloaddition

被引：17
|
作者：
Petz, Susanne [1 ]
Wanner, Klaus T. [1 ]
机构：
[1] Univ Munich, Dept Pharm, Ctr Drug Res, D-81377 Munich, Germany
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 2013卷 / 19期
关键词：
Nitrogen heterocycles; Neurotransmitters; Amino acids; Photochemistry; Cycloaddition; STEREOSELECTIVE-SYNTHESIS; ABSOLUTE STEREOCHEMISTRY; GABA UPTAKE; CYCLOADDITION; INHIBITORS; LACTONES; OLEFINS;
D O I：
10.1002/ejoc.201201723
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The synthesis of 3-azabicyclo[3.2.0]heptane-6-carboxylic acid and 7-substituted derivatives was developed as bicyclic analogues of -aminobutyric acid. A sensitized, intermolecular [2+2] photocycloaddition of maleic anhydride with N-protected 3-pyrroline served as the key step in these syntheses. Upon transformation of the anhydride function of the primary cycloaddition product, 6-monosubstituted and 6,7-disubstituted 3-azabicyclo[3.2.0]heptane derivatives were obtained.
引用
收藏
页码：4017 / 4025
页数：9
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