COPPER-MEDIATED OXIDATIVE CYCLIZATION OF HETEROCYCLICALLY SUBSTITUTED ALDIMINES

被引：6

作者：

Pufky-Heinrich, Daniela ^{[2
]}

Ciesielski, Michael ^{[1
]}

Gharnati, Loubna ^{[1
]}

Walter, Olaf ^{[1
]}

Doering, Manfred ^{[1
]}

机构：

[1] KIT, Inst Tech Chem ITC CPV, D-76021 Karlsruhe, Germany

[2] Univ Stuttgart, Inst Tech Chem, D-70550 Stuttgart, Germany

来源：

HETEROCYCLES | 2010年 / 81卷 / 08期

关键词：

Heterocyclization; Copper; Aldimine; Cycloaddition; Polycycle; DIELS-ALDER REACTIONS; AZOMETHINE YLIDES; CYCLOADDITION; COMPLEXES; ALKENES; ALKYNES;

D O I：

10.3987/COM-10-11966

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

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.

引用

页码：1811 / 1825

页数：15

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