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Synthesis 2009(13): 2143-2145  
DOI: 10.1055/s-0029-1216817
SHORTPAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Novel and Convenient Synthesis of ‘Reversed’ Diamidino 2,5-Aryl- and 2,5-Azaheterocycle-Substituted Furans

Laixing Hu, David W. Boykin*
Department of Chemistry, Georgia State University, Atlanta, GA 30303, USA
Fax: +1(404)4135505; e-Mail: dboykin@gsu.edu;
Further Information

Publication History

Received 12 January 2009
Publication Date:
14 May 2009 (online)

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Abstract

A novel and convenient two-step synthesis of ‘reversed’ diamidino 2,5-aryl- and 2,5-azaheterocycle-substituted furans is described. The key step, a Stille cross-coupling reaction between N-(bromoaryl)arenecarboxamidines and 2,5-bis(tri-n-butylstannyl)furan, is reported for the first time.

Key words

reversed amidines - thioimidates - Stille cross-coupling reaction - furans - N-heterocycles

    References

  • 1 Stephens CE. Tanious F. Kim S. Wilson WD. Schell WA. Perfect JR. Franzblau SG. Boykin DW. J. Med. Chem.  2001,  44:  1741 
    Google Scholar
  • 2 Stephens CE. Brun R. Salem MM. Werbovetz KA. Tanious F. Wilson WD. Boykin DW. Bioorg. Med. Chem. Lett.  2003,  13:  2065 
    CrossrefGoogle Scholar
  • 3a Silva CF. Meuser MB. De Souza EM. Meirelles MNL. Stephens CE. Som P. Boykin DW. Soeiro MNC. Antimicrob. Agents Chemother.  2007,  51:  3803 
    Google Scholar
  • 3b Silva CF. Batista MM. Mota RA. De Souza EM. Stephens CE. Som P. Boykin DW. Soeiro MNC. Biochem. Pharmacol.  2007,  73:  1939 
    Google Scholar
  • 3c Rosypal AC. Hall JE. Bakunova S. Patrik DA. Bakunov S. Stephens CE. Kumar A. Boykin DW. Tidwell RR. Vet. Parasitol.  2007,  145:  207 
    Google Scholar
  • 4 Kumar A. Stephens CE. Boykin DW. Heterocycl. Commun.  1999,  5:  301 
    Google Scholar
  • 5 Shearer BG. Oplinger JA. Lee S. Tetrahedron Lett.  1997,  38:  179 
    CrossrefGoogle Scholar
  • 6 Taylor EC. Zoltewicz JA. J. Am. Chem. Soc.  1960,  82:  2656 
    CrossrefGoogle Scholar
  • 7 Hisano T. Tasaki M. Tsumoto K. Matsuoka T. Ichikawa M. Chem. Pharm. Bull.  1983,  31:  2484 
    CrossrefGoogle Scholar
  • 8 Khanna IK. Weier RM. Yu Y. Xu XD. Koszyk FJ. Collins PW. Koboldt CM. Veenhuizen AW. Perkins WE. Casler JJ. Masferrer JL. Zhang YY. Gregory SA. Seibert K. Isakson PC. J. Med. Chem.  1997,  40:  1634 
    CrossrefGoogle Scholar
  • 9 Khanna IK. Yu Y. Huff RM. Weier RM. Xu X. Koszyk FJ. Collins PW. Cogburn JN. Isakson PC. Koboldt CM. Masferrer JL. Perkins WE. Seibert K. Veenhuizen AW. Yuan J. Yang DC. Zhang YY. J. Med. Chem.  2000,  43:  3168 
    Google Scholar
  • 10 Lange JHM. van Stuivenberg HH. Coolen HKAC. Adolfs TJP. McCreary AC. Keizer HG. Wals HC. Veerman W. Borst AJM. de Looff W. Verveer PC. Kruse CG. J. Med. Chem.  2005,  48:  1823 
    CrossrefGoogle Scholar