Synthesis of polyfunctional indoles and related heterocycles mediated by cesium and potassium bases

A general preparation of 2-substituted indoles starting from functionalized 2-alkynylanilines has been developed. This base mediated reaction has also been used to synthesize the heterocyclic core of the marine alkaloid hinckdentine A. Furthermore the reaction was successfully adapted to the solid p...

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Bibliographic Details
Published in:Tetrahedron 2003-02, Vol.59 (9), p.1571-1587
Main Authors: Koradin, Christopher, Dohle, Wolfgang, Rodriguez, Alain L, Schmid, Bertram, Knochel, Paul
Format: Article
Language:English
Subjects:
cesium and potassium bases
cyclization
heterocycles
indoles
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Summary:A general preparation of 2-substituted indoles starting from functionalized 2-alkynylanilines has been developed. This base mediated reaction has also been used to synthesize the heterocyclic core of the marine alkaloid hinckdentine A. Furthermore the reaction was successfully adapted to the solid phase. Benzofurans and isoindolones could also be prepared with this method. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(03)00073-5