Synthesis 2010(10): 1625-1628  
DOI: 10.1055/s-0029-1218703
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

An Efficient New Method for the Synthesis of Polysubstituted Pyrroles [¹]

Biswanath Das*, Gandolla Chinna Reddy, Penagaluri Balasubramanyam, Boyapati Veeranjaneyulu
Organic Chemistry Division-1, Indian Institute of Chemical Technology, Hyderabad 500 007, India
Fax: +91(40)27193198; e-Mail: biswanathdas@yahoo.com;
Weitere Informationen

Publikationsverlauf

Received 1 February 2010
Publikationsdatum:
15. März 2010 (online)

Abstract

The three-component reactions of phenacyl bromide or its derivatives, amine, and dialkyl acetylenedicarboxylate in the presence of iron(III) chloride as a catalyst at room temperature afforded polysubstituted pyrroles in high yields.

1

Part 283 in the series ‘Studies on Novel Synthetic Methodologies’.

    References

  • 2a Finar IL. Organic Chemistry: Stereochemistry and Chemistry of Natural Products   5th ed., Vol. 2:  Longman; London: 1975.  p.885-913  
  • 2b O’Hagan D. Nat. Prod. Rep.  2000,  17:  435 
  • 2c Walsh CT. Garneau-Tsodikova S. Howard-Jones AR. Nat. Prod. Rep.  2006,  23:  517 
  • 3a Huffman JW. Curr. Med. Chem.  1999,  6:  705 
  • 3b Kidwai M. Venkataramanan R. Mohan R. Sapra P. Curr. Med. Chem.  2002,  9:  1209 
  • 3c La Regina G. Silvestri R. Artico M. Lavechia A. Novellino E. Befani O. Turini P. Agostinelli E. J. Med. Chem.  2007,  50:  922 
  • 4a Boger DL. Boyce CW. Labrilli MA. Sehon CA. Jin Q. J. Am. Chem. Soc.  1999,  121:  54 
  • 4b Abid M. Landge SM. Torok B. Org. Prep. Proced. Int.  2006,  38:  495 
  • 5a Facchetti A. Abboto A. Beverina L. van der Boom ME. Dutta P. Evmenenko G. Pagani GA. Marks TJ. Chem. Mater.  2003,  15:  1064 
  • 5b Pu S. Liu G. Shen L. Xu J. Org. Lett.  2007,  9:  2139 
  • Some recent examples:
  • 6a Larionov OV. de Meijere A. Angew. Chem. Int. Ed.  2005,  44:  5664 
  • 6b Minetto G. Raveglia LF. Sega A. Taddei M. Eur. J. Org. Chem.  2005,  24:  5277 
  • 6c Shiner CM. Laner TD. Tetrahedron  2005,  61:  11628 
  • 6d Hwang SJ. Cho SH. Chang S.
    J. Am. Chem. Soc.  2008,  130:  16158 
  • 6e Abid M. Teixeira L. Torok B. Org. Lett.  2008,  10:  933 
  • 6f La YD. Arndtsen BA. Angew. Chem. Int. Ed.  2008,  47:  5430 
  • 7a Das B. Balasubramanyam P. Krishnaiah M. Veeranjaneyulu B. Reddy GC. J. Org. Chem.  2009,  74:  4393 
  • 7b Das B. Damodar K. Bhunia N. J. Org. Chem.  2009,  74:  5607 
  • 7c Das B. Satyalakshmi G. Suneel K. Damodar K. J. Org. Chem.  2009,  74:  8400 
  • 7d Das B. Balasubramanyam P. Veeranjaneyulu B. Reddy GC.
    J. Org. Chem.  2009,  74:  9505 
  • 8 Zhu Q. Jiang H. Li J. Zhang M. Wang X. Qi C. Tetrahedron  2009,  65:  4604 
1

Part 283 in the series ‘Studies on Novel Synthetic Methodologies’.