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COPPER-MEDIATED OXIDATIVE CYCLIZATION OF HETEROCYCLICALLY SUBSTITUTED ALDIMINES

  作者 PUFKYHEINRICH DANIELA; CIESIELSKI MICHAEL; GHARNATI LOUBNA; WALTER OLAF; DOERING MANFRED  
  选自 期刊  Heterocycles;  卷期  2010年81-8;  页码  1811-1825  
  关联知识点  
 

[摘要]Copper-mediated cascade reactions were performed with heterocyclically substituted aldimines. These oxidative heterocyclizations include sequences of oxidations and cycloadditions or nucleophilic additions which take place in the coordination sphere of copper ions. When two heterocyclically substituted aldimines were reacted in the presence of copper (II) salts under air, pyridine derivatives were produced. In one case a 1,4-diazatricyclo-[3.2.1.0(2,7)]oct-3-ene was also formed. The basic structure of this new tetracyclic compound contains five new chirale carbon atoms. This cage-like structure has been revealed by X-ray crystallography. The synthesis of 2H-pyrroles by copper-assisted conversions of the aldimines with dimethylacetylene carboxylate or quinones was also described.

 
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