Coupling of beta-cyanocarbene-chromium complexes with 2-alkynylbenzoyl derivatives: A [5+5]-cycloaddition approach to phenanthridines

The coupling of beta-cyanocarbene complexes and 2-alkynylbenzoyl derivatives has been examined. The reaction afforded phenanthridine derivatives in a complex tandem process involving carbene-alkyne coupling, isobenzofuran formation, intramolecular Diels-Alder reaction using a nitrite dienopbile, and...

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Bibliographic Details
Published inSynthesis (Stuttgart) no. 21; pp. 3661 - 3669
Main Authors Ghorai, Binay K., Duan, Shaofeng, Jiang, Delu, Herndon, James W.
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 03.11.2006
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
Diels-Alder reactions
FISCHER CARBENE COMPLEXES
chromium
alkynes
CHEMISTRY
cycloadditions
nitrites
SALTS
carbene complexes
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Summary:The coupling of beta-cyanocarbene complexes and 2-alkynylbenzoyl derivatives has been examined. The reaction afforded phenanthridine derivatives in a complex tandem process involving carbene-alkyne coupling, isobenzofuran formation, intramolecular Diels-Alder reaction using a nitrite dienopbile, and deoxygenation. The chemistry could not be reproduced in non-chromium-based systems.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-2006-950286