Solvent-Free Indoles Addition to Carbonyl Compounds Promoted by CeCl3·7H2O-NaI-SiO2: An Efficient Method for the Synthesis of Streptindole

Giuseppe Bartoli; Marcella Bosco; Gioia Foglia; Arianna Giuliani; Enrico Marcantoni; Letizia Sambri

doi:10.1055/s-2004-815967

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Synthesis 2004(6): 895-900
DOI: 10.1055/s-2004-815967

PAPER

Solvent-Free Indoles Addition to Carbonyl Compounds Promoted by CeCl₃·7H₂O-NaI-SiO₂: An Efficient Method for the Synthesis of Streptindole

Giuseppe Bartoli^a, Marcella Bosco^a, Gioia Foglia^b, Arianna Giuliani^b, Enrico Marcantoni*^b, Letizia Sambri^a
^a Dipartimento di Chimica Organica ‘A. Mangini’, Università di Bologna, v.le Risorgimento 4, 40136 Bologna Italy
^b Dipartimento di Scienze Chimiche, Università di Camerino, v. S. Agostino 1, 62032 Camerino (MC), Italy
Fax: +39(0737)402297; e-Mail: enrico.marcantoni@unicam.it.it;

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Publication History

Received 7 January 2004
Publication Date:
10 February 2004 (online)

Abstract
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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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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.