Synthesis 2006(1): 81-88  
DOI: 10.1055/s-2005-921757
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Novel Diethyl Indolylphosphonates and Tetraethyl Indolyl-1,1-bisphosphonates by Michael Addition

Hélène Couthon-Gourvès*, Gaëlle Simon, Jean-Pierre Haelters, Bernard Corbel
Laboratoire de Chimie Hétéro-Organique, U.F.R. Sciences et Techniques, 6. av. Le Gorgeu - C.S. 93837, 29238 Brest Cedex 3, France
Fax: +33(2)98016704; e-Mail: Helene.Couthon@univ-brest.fr;
Further Information

Publication History

Received 14 April 2005
Publication Date:
16 December 2005 (online)

Abstract

As series of (1H-indol-3-yl)phosphonates and bisphosphonates as well as (1H-indol-1-yl)phosphonates and bisphosphonates was prepared via the Michael addition of substituted indoles with electron-deficient olefins like ethyl 2-(diethoxyphosphoryl)acrylate and tetraethyl ethenylidene-1,1-bisphosphonate. The chemoselectivity of the reaction is discussed.

    References

  • 1 Sundberg RJ. The Chemistry of Indoles   Academic Press; New York: 1996. 
  • 2a Engel R. Synthesis of Carbon-Phosphorus Bonds   CRC Press; Boca Raton /FL: 1988. 
  • 2b Engel R. Chem. Rev.  1977,  77:  349 
  • 2c Hori T. Horiguchi M. Hayashi A. Biochemistry of Natural C-P Compounds   Maruzen, Kyoto Branch Publishing Service; Kyoto: 1984. 
  • 3 Fleisch H. Bisphosphonates in Bone Disease   4th ed.:  Academic Press; New York: 2000. 
  • 4 Neville-Webbe HL. Holen I. Coleman RE. Cancer Treat. Rev.  2002,  28:  305 
  • 5a Russel RG. Smith R. Preston C. Walton RJ. Woods C. Lancet  1974,  1:  894 
  • 5b Delmas P. Meunier P. N. Engl. J. Med.  1997,  336:  558 
  • 6 Francis RM. Curr. Ther. Res.  1997,  58:  656 
  • 7 Widler L. Jaeggi KA. Glatt M. Müller K. Bachmann R. Bisping M. Born AR. Cortesi R. Guiglia G. Heidi J. Klein R. Ramseier U. Schmid J. Schreiber G. Seltenmeyer Y. Green JR. J. Med. Chem.  2002,  45:  3721 
  • 8a Haelters JP. Corbel B. Sturtz G. C. R. Acad. Sci. II  1985,  301:  697 
  • 8b Haelters JP. Corbel B. Sturtz G. Phosphorus Sulfur Relat. Elem.  1988,  37:  41 
  • 8c Haelters JP. Corbel B. Sturtz G. Phosphorus Sulfur Relat. Elem.  1988,  37:  65 
  • 8d Sturtz G. Guervenou J. Synthesis  1991,  661 
  • 8e Gourves JP. Couthon H. Sturtz G. Phosphorus, Sulfur Silicon Relat. Elem.  1998,  132:  219 
  • 8f Couthon H. Gourves JP. Guervenou J. Corbel B. Sturtz G. Synth. Commun.  1999,  29:  4251 
  • 8g Guervenou J. Gourves JP. Couthon H. Corbel B. Sturtz G. Kervarec N. Phosphorus, Sulfur Silicon Relat. Elem.  2000,  156:  107 
  • 8h Guervenou J. Couthon-Gourves H. Gourves JP. Corbel B. Synth. Commun.  2002,  32:  1543 
  • 8i Ruzziconi R. Ricci G. Gioiello A. Couthon-Gourves H. Gourves JP. J. Org. Chem.  2003,  68:  736 
  • 9a Poupaert JH. Bukuru J. Gozzo A. Monatsh. Chem.  1999,  130:  929 
  • 9b Macor JE. Blank DH. Ryan K. Post RJ. Synthesis  1997,  443 
  • 9c Harrington P. Kerr MA. Can. J. Chem.  1998,  76:  1256 
  • 9d Harrington P. Kerr MA. Synlett  1996,  1047 
  • 9e Yadav JS. Abraham S. Reddy BVS. Sabitha G. Synthesis  2001,  2165 
  • 10 Krawczyk H. Sliwinski M. Synthesis  2002,  1351 
  • 11 Degenhardt CR. Burdsall DC. J. Org. Chem.  1986,  51:  3488 
  • 12 Ottoni O. Cruz R. Alves R. Tetrahedron  1998,  54:  13915