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Synlett 2011(16): 2384-2386  
DOI: 10.1055/s-0030-1261236
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Microwave-Enhanced Reaction of Thioacids with Azides in Aqueous Medium

Pallavi Sharma, Adam D. Moorhouse, John E. Moses*
School of Chemistry, University of Nottingham, University Park, Nottingham, NG7 2RD, UK
Fax: +44(115)9513564; e-Mail: john.moses@nottingham.ac.uk;
Further Information

Publication History

Received 20 July 2011
Publication Date:
13 September 2011 (online)

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Abstract

An efficient entry to aromatic amides using microwave irradiation in aqueous medium is described. Starting from substituted anilines, in situ formation of the corresponding aromatic azide is followed by their immediate reaction with a thioacid to yield amides in excellent yield. This improved protocol significantly reduces the reaction time thus increasing the overall efficiency of this useful transformation.

Key words

aromatic amides - azides - thio acids - microwave - one pot

    References and Notes

  • 1 Bräse S. Gil C. Knepper K. Zimmermann V. Angew. Chem. Int. Ed.  2005,  44:  5188 
    CrossrefPubMedGoogle Scholar
  • 2a Moorhouse AD. Spiteri C. Sharma P. Zloh M. Moses JE. Chem. Commun.  2011,  47:  230 
    Google Scholar
  • 2b Gunaratnam M. Green C. Moreira JB. Moorhouse AD. Kelland LR. Moses JE. Neidle S. Biochem. Pharm.  2009,  78:  115 
    Google Scholar
  • 2c Moorhouse AD. Haider S. Gunaratnam M. Munnur D. Neidle S. Moses JE. Mol. BioSyst.  2008,  4:  629 
    Google Scholar
  • 2d Moorhouse AD. Moses JE. ChemMedChem  2008,  3:  715 
    Google Scholar
  • 2e Moorhouse AD. Santos AM. Gunaratnam M. Moore M. Neidle S. Moses JE. J. Am. Chem. Soc.  2006,  128:  15972 
    Google Scholar
  • 3 Hang HC. Bertozzi CR. Acc. Chem. Res.  2001,  34:  727 
    CrossrefGoogle Scholar
  • 4a Moses JE. Moorhouse AD. Chem. Soc. Rev.  2007,  36:  1249 
    Google Scholar
  • 4b Rostovtsev VV. Green LG. Fokin VV. Sharpless KB. Angew. Chem. Int. Ed.  2002,  41:  2596 
    Google Scholar
  • 5 Kolb HC. Finn MG. Sharpless KB. Angew. Chem. Int. Ed.  2001,  40:  2004 
    CrossrefPubMedGoogle Scholar
  • 6 Barral K. Moorhouse AD. Moses JE. Org. Lett.  2007,  9:  1809 
    CrossrefPubMedGoogle Scholar
  • 7 Rosen T. Lico IM. Chu DTW. J. Org. Chem.  1988,  53:  1580 
    CrossrefGoogle Scholar
  • 8a Kolakowski RV. Shangguan N. Sauers RR. Williams LJ. J. Am. Chem. Soc.  2006,  128:  5695 
    Google Scholar
  • 8b Shangguan N. Katukojvala S. Greenberg R. Williams LJ. J. Am. Chem. Soc.  2003,  125:  7754 
    Google Scholar
  • 9 Montalbetti CAGN. Falque V. Tetrahedron  2005,  61:  10827 
    CrossrefGoogle Scholar
  • 10a Nájera C. Yus M. In Studies in Natural Products Chemistry   Vol. 21:  . Elsevier Science; Amsterdam: 2000.  p.373 
    Google Scholar
  • 10b Wipf P. Chem. Rev.  1995,  95:  2115 
    Google Scholar
  • 11a Zhang F. Moses JE. Org. Lett.  2009,  11:  1587 
    Google Scholar
  • 11b Moorhouse AD. Moses JE. Synlett  2008,  2089 
    Google Scholar