Download PDF
Synthesis 2006(24): 4247-4251  
DOI: 10.1055/s-2006-950360
PAPER
© Georg Thieme Verlag Stuttgart · New York

An Easy and Convenient Synthesis of 2-Furan-2-ylacetamides by Sequential Palladium-Catalyzed Oxidative Aminocarbonylation of (Z)-2-En-4-yn-1-ols/Conjugate Addition/Aromatization

Bartolo Gabriele*a, Pierluigi Plastinab, Giuseppe Salernob, Raffaella Mancusob
a Dipartimento di Scienze Farmaceutiche, Università della Calabria, 87036 Arcavacata di Rende (Cosenza), Italy
Fax: +39(0984)492044; e-Mail: b.gabriele@unical.it;
b Dipartimento di Chimica, Università della Calabria, 87036 Arcavacata di Rende (Cosenza), Italy
Further Information

Publication History

Received 31 July 2006
Publication Date:
02 November 2006 (online)

    Permissions and Reprints All articles of this category

Abstract

A simple and convenient synthesis of 2-furan-2-ylacet­amides 4 starting from readily available (Z)-2-en-4-yn-1-ols 1 is reported. The method is based on a PdI2-catalyzed oxidative aminocarbonylation of the triple bond of 1 to give the corresponding 2-ynamide intermediates 2, which undergo intramolecular conjugate addition to give 2-(5H-furan-2-ylidene)acetamide derivatives 3. Spontaneous or one-pot acid-promoted aromatization of 3 eventually leads to the final furanacetamide derivatives 4.

Key words

aminocarbonylation - furans - 2-furan-2-ylacetamides - palladium

    References

  • 1 Gabriele B. Salerno G. Veltri L. Costa M.
    J. Organomet. Chem.  2001,  622:  84 
    CrossrefGoogle Scholar
  • 2 Gabriele B. Salerno G. Plastina P. Costa M. Crispini A. Adv. Synth. Catal.  2004,  346:  351 
    CrossrefGoogle Scholar
  • 3 Gabriele B. Salerno G. Plastina P. Lett. Org. Chem.  2004,  1:  134 
    CrossrefGoogle Scholar
  • 4 Gabriele B. Plastina P. Salerno G. Costa M. Synlett  2005,  935 
    Article in Thieme ConnectGoogle Scholar
  • 5 Gabriele B. Salerno G. Mancuso R. Costa M. J. Org. Chem.  2004,  69:  4741 
    CrossrefGoogle Scholar
  • 6 Gabriele B. Salerno G. Lauria E. J. Org. Chem.  1999,  64:  7687 
    Google Scholar
  • 7a Shen M. Beguin C. Golbraikh A. Stables JP. Kohn H. Tropsha A. J. Med. Chem.  2004,  47:  2356 
    Google Scholar
  • 7b Prasad CVC. Shikha V. Smith DW. Gao Q. Polson CT. Corsa JA. Guss VL. Loo A. Barten DM. Zheng M. Felsenstein KM. Roberts SB. Bioorg. Med. Chem. Lett.  2004,  14:  3535 
    Google Scholar
  • 7c Sheehan SM. Masters JJ. Wiley MR. Young SC. Liebeschuetz JW. Jones SD. Murray CW. Franciskovich JB. Engel DB. Weber WW. Marimuthu J. Kyle JA. Smallwood JK. Farmen MW. Smith GF. Bioorg. Med. Chem. Lett.  2003,  13:  2255 
    Google Scholar
  • 7d Shen M. LeTiran A. Xiao Y. Golbraikh A. Kohn H. Tropsha A. J. Med. Chem.  2002,  45:  2811 
    Google Scholar
  • 7e Li Z. Yeo SL. Pallen CJ. Ganesan A. Bioorg. Med. Chem. Lett.  1998,  8:  2443 
    Google Scholar
  • 7f Stewart AO. Bhatia PA. Martin JG. Summers JB. Rodriques KE. Martin MB. Holms JH. Moore JL. Craig RA. Kolasa T. Ratajczyk JD. Mazdiyasni H. Kerdesky FAJ. DeNinno SL. Maki RG. Bouska JB. Young PR. Lanni C. Bell RL. Carter GW. Brooks CDW. J. Med. Chem.  1997,  40:  1955 
    Google Scholar
  • 7g Kohn H. Sawhney KN. Bardel P. Robertson DW. Leander JD. J. Med. Chem.  1993,  36:  3350 
    Google Scholar
  • 7h Kohn H. Sawhney KN. LeGall P. Robertson DW. Leander JD. J. Med. Chem.  1991,  34:  2444 
    Google Scholar
  • 7i Vansdadia RN. Roda KP. Parekh H. J. Indian Chem. Soc.  1989,  66:  110 
    Google Scholar
  • 7j Kohn H. Sawhney KN. LeGall P. Conley JD. Robertson DW. Leander JD. J. Med. Chem.  1990,  33:  919 
    Google Scholar
  • 7k Shah VH. Patel HH. Parikh AR. J. Indian Chem. Soc.  1982,  59:  678 
    Google Scholar
  • 8 Wang S.-H. Tu Y.-Q. Chen P. Hu X.-D. Zhang F.-M. Wang A.-X. J. Org. Chem.  2006,  71:  4343 
    CrossrefGoogle Scholar