Catalytic Cyclization of o-Alkynyl Phenethylamines via Osmacyclopropene Intermediates: Direct Access to Dopaminergic 3-Benzazepines

被引：37
作者：
Alvarez-Perez, Andrea [1 ,2 ]
Gonzalez-Rodriguez, Carlos [1 ,2 ]
Garcia-Yebra, Cristina [3 ]
Varela, Jesus A. [1 ,2 ]
Onate, Enrique [3 ]
Esteruelas, Miguel A. [3 ]
Saa, Carlos [1 ,2 ]
机构：
[1] Univ Santiago de Compostela, Dept Quim Organ, Santiago De Compostela 15782, Spain
[2] Univ Santiago de Compostela, Ctr Singular Invest Quim Biol & Mat Mol CIQUS, Santiago De Compostela 15782, Spain
[3] Univ Zaragoza, CSIC, Ctr Innovac Quim Avanzada ORFEO CINQA, Dept Quim Inorgan,Inst Sintesis Quim & Catalisis, E-50009 Zaragoza, Spain
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2015年 / 54卷 / 45期
关键词：
benzazepines; cyclization; metallacyclopropenes; osmium catalysts; phenethylamines; INTRAMOLECULAR HYDROAMINATION; REGIOSELECTIVE SYNTHESIS; 2-SUBSTITUTED PYRIDINES; TERMINAL ALKYNES; OSMIUM COMPLEXES; RECENT PROGRESS; CHEMISTRY; RUTHENIUM; VINYLIDENE; HYDROAMIDATION;
D O I：
10.1002/anie.201505782
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A novel osmium-catalyzed cyclization of o-alkynyl phenethylamines to give 3-benzazepines is reported. The procedure allows the straightforward preparation of a broad range of dopaminergic 3-benzazepine derivatives. Mechanistic investigations revealed that the process takes place via osmacyclopropene intermediates, which were isolated and characterized by X-ray crystallography.
引用
收藏
页码：13357 / 13361
页数：5
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