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Synthesis 2009(13): 2143-2145
DOI: 10.1055/s-0029-1216817
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
Weitere Informationen
Received
12 January 2009
Publikationsdatum:
14. Mai 2009 (online)
Publikationsverlauf
Publikationsdatum:
14. Mai 2009 (online)
![](https://www.thieme-connect.de/media/synthesis/200913/lookinside/thumbnails/10.1055-s-0029-1216817-1.jpg)
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
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Stephens CE.Tanious F.Kim S.Wilson WD.Schell WA.Perfect JR.Franzblau SG.Boykin DW. J. Med. Chem. 2001, 44: 1741 - 2
Stephens CE.Brun R.Salem MM.Werbovetz KA.Tanious F.Wilson WD.Boykin DW. Bioorg. Med. Chem. Lett. 2003, 13: 2065 -
3a
Silva CF.Meuser MB.De Souza EM.Meirelles MNL.Stephens CE.Som P.Boykin DW.Soeiro MNC. Antimicrob. Agents Chemother. 2007, 51: 3803 -
3b
Silva CF.Batista MM.Mota RA.De Souza EM.Stephens CE.Som P.Boykin DW.Soeiro MNC. Biochem. Pharmacol. 2007, 73: 1939 -
3c
Rosypal AC.Hall JE.Bakunova S.Patrik DA.Bakunov S.Stephens CE.Kumar A.Boykin DW.Tidwell RR. Vet. Parasitol. 2007, 145: 207 - 4
Kumar A.Stephens CE.Boykin DW. Heterocycl. Commun. 1999, 5: 301 - 5
Shearer BG.Oplinger JA.Lee S. Tetrahedron Lett. 1997, 38: 179 - 6
Taylor EC.Zoltewicz JA. J. Am. Chem. Soc. 1960, 82: 2656 - 7
Hisano T.Tasaki M.Tsumoto K.Matsuoka T.Ichikawa M. Chem. Pharm. Bull. 1983, 31: 2484 - 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 - 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 - 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