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Synthesis 2006(9): 1494-1498  
DOI: 10.1055/s-2006-926426
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (E)-3-(1H-Pyrrol-3-yl)prop-2-ene Derivatives Using Organo­phosphorous Reagents

Nikolaos Karousisa, Jürgen Liebscher*b, George Varvounis*a
a Department of Chemistry, University of Ioannina, 45110 Ioannina, Greece
Fax: +30(265)1098799; e-Mail: gvarvoun@cc.uoi.gr;
b Institute für Chemie, Humboldt-Universität Berlin, Brook-Taylor-Strasse 2, 12489 Berlin, Germany
Fax: +49(30)20937552; e-Mail: liebscher@rz.hu-berlin.de;
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Publication History

Received 12 September 2005
Publication Date:
11 April 2006 (online)

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Abstract

The synthesis of (E)-3-[1-(toluene-4-sulfonyl)-1H-pyrrol-3-yl]prop-2-ene derivatives from 1-(toluene-4-sulfonyl)-1H-pyrrole-3-carbaldehyde by the Horner-Wadsworth-Emmons (HWE) reaction, is described. However, the HWE reaction with diethyl methoxymethylphosphonate and diethyl (2-methoxyethoxy)methylphosphonate gave a different product, namely, diethyl {1-methoxy(or methoxyethoxy)-2-[1-(toluene-4-sulfonyl)-1H-pyrrol-3-yl]vinyl}phosphonates, respectively. (E)-3-[1-(Toluene-4-sulfonyl)-1H-pyrrol-3-yl]prop-2-enes were easily hydrolysed to (E)-3-(1H-pyrrol-3-yl)prop-2-enes, two of which are natural products.

Key words

pyrroles - phosphonates - Horner-Wadsworth-Emmons reaction