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Synthesis 2004(6): 895-900
DOI: 10.1055/s-2004-815967
DOI: 10.1055/s-2004-815967
PAPER
© Georg Thieme Verlag Stuttgart · New York
Solvent-Free Indoles Addition to Carbonyl Compounds Promoted by CeCl3·7H2O-NaI-SiO2: An Efficient Method for the Synthesis of Streptindole
Further Information
Received
7 January 2004
Publication Date:
10 February 2004 (online)
Publication History
Publication Date:
10 February 2004 (online)
Abstract
Efficient electrophilic substitution reactions of indoles with various carbonyl compounds proceed easily in solvent-free conditions using CeCl3·7H2O-NaI-SiO2 system promoter, to afford the corresponding bis(1H-indol-3-yl)alkanes in high yields. The synthetic value of the present procedure is demonstrated by the synthesis of streptindole (9), human intestinal bacteria metabolite.
Key words
addition reactions - carbonyl complexes - indoles - lanthanides - Lewis acids - natural products
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References
In our methodology of Lewis acid promoted solvent-free reaction the term ‘solvent-free’ refers solely to the reaction itself. On the other hand, preparation of initial adsorbate and purification of products invariably involve the use of solvent.