An Expedient Construction of Seven-Membered Rings Adjoining Aromatic Systems

An unusual radical‐mediated fusion of a seven‐membered ring onto an aromatic system exploits the relatively long lifetime of radicals generated using dithiocarbonates (xanthates). This type of annelation (an example is shown), which was hitherto very difficult to accomplish by more traditional radic...

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Bibliographic Details
Published inAngewandte Chemie (International ed.) Vol. 39; no. 4; pp. 731 - 733
Main Authors Kaoudi, Talbi, Quiclet-Sire, Béatrice, Seguin, Stéphanie, Zard, Samir Z.
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag GmbH 18.02.2000
WILEY‐VCH Verlag GmbH
Wiley
Wiley-VCH Verlag
Subjects
annulations
Chemical Sciences
Chemistry
Chemistry, Multidisciplinary
C−C coupling
Organic chemistry
Physical Sciences
radical reactions
Science & Technology
xanthates
C-C coupling
ORGANIC-SYNTHESIS
DESIGN
ACID
radical reactions
ALPHA
RADICAL CHAIN REACTIONS
1,2-FUSED INDOLES
annulations
xanthates
TRYPTOPHAN DERIVATIVES
PHOTOCYCLIZATION
CYCLIZATION
ALKALOIDS
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Summary:An unusual radical‐mediated fusion of a seven‐membered ring onto an aromatic system exploits the relatively long lifetime of radicals generated using dithiocarbonates (xanthates). This type of annelation (an example is shown), which was hitherto very difficult to accomplish by more traditional radical methods, was used to construct a variety of complex structures. Y=OAc, CN, (CH2)8OAc, CH2CO2Et, phthaloyl.
Bibliography:istex:1190F6AEACBEBB3B23909801AD7215F3EDC66FC9
ark:/67375/WNG-DMWHP65N-F
ArticleID:ANIE731
We wish to thank the Ligue Contre le Cancer for generous financial support for S.S. and Michel Levart for recording numerous GC mass spectra.
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ISSN:1433-7851
1521-3773
DOI:10.1002/(SICI)1521-3773(20000218)39:4<731::AID-ANIE731>3.0.CO;2-U