Synthesis 2004(6): 895-900  
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

Giuseppe Bartolia, Marcella Boscoa, Gioia Fogliab, Arianna Giulianib, Enrico Marcantoni*b, Letizia Sambria
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;
Further Information

Publication History

Received 7 January 2004
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.

17

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.