Cobalt-mediated [2+2+2] cycloaddition versus C-H and N-H activation of pyridones and pyrazinones with alkynes: An experimental study

被引：53

作者：

Aubert, Corinne

Betschmann, Patrick

Eichberg, Michael J.

Gandon, Vincent

Heckrodt, Thilo J.

Lehmann, Juerg

Malacria, Max

Masjost, Birgit

Paredes, Elisa

Vollhardt, K. Peter C.

Whitener, Glenn D.

机构：

[1] Univ Paris 06, UMR CNRS 7611, Inst Chem Mol, Lab Chem Organ, F-75252 Paris, France

[2] Univ Calif Berkeley, Dept Chem, Lawrence Berkeley Natl Lab, Div Chem Sci, Berkeley, CA 94720 USA

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2007年 / 13卷 / 26期

关键词：

C-H activation; cobalt cycloaddition; heterocycles; N-H activation;

D O I：

10.1002/chem.200601823

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The reactivity of a range of pyridone and pyrazinone derivatives towards alkynes in the presence of cyclopentadienylcobaltbis(ethene) has been investigated. Depending on the nature of the substrates, [2+2+2]- or [2+2] cycloaddition, C-H, or N-H activation may occur. In the case of pyridones, the first three predominated with N-protected derivatives, whereas substrates containing N-H bonds followed an N-H activation pathway. The [2+2+2] cycloaddition of an N-buty-nylisoquinolone was applied successfully to the total synthesis of anhydrolycorinone. Pyrazinone substrates showed similar patterns of reactivity.

引用

页码：7443 / 7465

页数：23

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[31] THE PREPARATION OF 2(1H)-PYRIDINONES AND 2,3-DIHYDRO-5(1H)-INDOLIZINONES VIA TRANSITION-METAL MEDIATED COCYCLIZATION OF ALKYNES AND ISOCYANATES - A NOVEL CONSTRUCTION OF THE ANTITUMOR AGENT CAMPTOTHECIN [J].