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Paper | Regular issue | Vol 81, No. 8, 2010, pp.1811-1825
Published online, 21st June, 2010
DOI: 10.3987/COM-10-11966
Copper-Mediated Oxidative Cyclization of Heterocyclically Substituted Aldimines

Daniela Pufky-Heinrich, Michael Ciesielski, Loubna Gharnati, Olaf Walter, and Manfred Döring*

*Institute of Catalysis Research and Technology, Karlsruhe Institute of Technology, Hermann-von-Helmholtz Platz 1, 76344 Eggenstein-Leopoldshafen, Germany


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-[,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.