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;
Further Information

Publication History

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

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.

    References

  • 1 Gribble GW. In Comprehensive Heterocyclic Chemistry II   Vol. 2:  Katritzky AR. Rees CW. Scriven EFV. Pergamon; Oxford: 1996.  p.207 
  • 2 Keller-Schierlein W. Muller A. Hagmann L. Schneider U. Zahner H. Helv. Chim. Acta  1985,  68:  559 
  • 3 Labouta IM. Jacobsen P. Thorbek P. Krogsgaard-Larsen P. Hjeds H. Acta Chem. Scand. B  1982,  36:  669 
  • 4 Carter P. Fitzjohn S. Halazy S. Magnus P. J. Am. Chem. Soc.  1987,  109:  2711 
  • 5 Nishikawa Y. Shindo T. Ishii K. Nakamura H. Kon T. Uno H. Chem. Pharm. Bull.  1989,  37:  684 
  • 6 Gosney I. Rowley AG. In Organophosphorus Reagents in Organic Synthesis   Cadogan JIG. Academic Press; London: 1979.  p.17-153  
  • 7 Carson JR. Davis NM. J. Org. Chem.  1981,  46:  839 
  • 8a Anderson HJ. Clase A. Loader CE. Synth. Commun.  1987,  17:  401 
  • 8b Demopoulos V. Org. Prep. Proced. Int.  1986,  18:  278 
  • 9 Bray BL. Mathies PH. Naef R. Solas DR. Tidwell TT. Artis DR. Muchowski JM. J. Org. Chem.  1990,  55:  6317 
  • 10a Kakushima M. Hamel P. Frennete R. Rokach J. J. Org. Chem.  1983,  48:  3214 
  • 10b Xiao D. Ketcha DM. Org. Prep. Proced. Int.  1995,  27:  503 
  • 11a Plieninger H. El Berins R. Hirsch R. Synthesis  1973,  422 
  • 11b Hamdan A. Wasley JWF. Synth. Commun.  1983,  13:  741 
  • 12 Landor PD. Landor SR. Odyek O. J. Chem. Soc., Perkin Trans. 1  1977,  93 
  • 13 Dawson ND. Burger A. J. Am. Chem. Soc.  1952,  74:  5312 
  • 14 Tsunkawa M. Kamei H. Konishi M. Miyaki T. Oki T. Kawagushi H. J. Antibiot.  1988,  41:  1366 
  • 15 Kluge AF. Clousdale IS. J. Org. Chem.  1979,  44:  4847 
  • 16 Ruiz M. Fernandez MC. Diaz A. Quintela JM. Ojea V. J. Org. Chem.  2003,  68:  7634 
  • 17 Demopoulos V. J. Heterocycl. Chem.  1988,  25:  635