RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
          
          https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000083.xml
        Synlett  2005(8): 1251-1254  
DOI: 10.1055/s-2005-868481
   DOI: 10.1055/s-2005-868481
LETTER
© Georg Thieme Verlag Stuttgart · New YorkA Facile Route to Sterically Hindered and Non-Hindered 4′-Aryl-2,2′:6′,2′′-Terpyridines
Weitere Informationen
            
               
                  
                        
                              Received
                              11 February 2005 
                      
Publikationsdatum:
21. April 2005 (online)
            
         
      
   Publikationsverlauf
Publikationsdatum:
21. April 2005 (online)
Abstract
A facile one-pot synthesis of 4′-aryl-2,2′:6′,2′′-terpyridines from aryl aldehydes and 2-acetylpyridine is presented. The synthesis of terpyridines incorporating sterically hindered aryl groups, such as the 9-anthryl group, can also be readily synthesized using this method.
Key words
nitrogen ligands - heterocycles - substituted terpyridines - one-pot reactions
- 1a 
             
            
Demas JM.DeGra BA. Coord. Chem. Rev. 2001, 211: 317 - 1b For a recent example:  
            
Kimura M.Takahashi A.Sakata T.Tsukahara K. Bull. Chem. Soc. Jpn. 1998, 71: 1839 - 1c 
             
            
Péchy P.Rotzinger FP.Nazeeruddin MK.Kohle O.Zakeeruddin SM.Humphry-Baker R.Grätzel M. J. Chem. Soc., Chem. Commun. 1995, 65 - 1d 
             
            
Baldo MA.Thompson ME.Forrest SR. Nature 2000, 403: 750 - 1e 
             
            
Ziessel RJ. Inclusion Phenom. Macrocyclic Chem. 1999, 35: 369 - 2 
             
            
Constable EC.Cargill Thompson AMW.Tocher DA.Daniels MAM. New J. Chem. 1992, 16: 855 - 3 
             
            
Sauvage J.-P.Collin J.-P.Chambron J.-C.Guillerez S.Coudret C.Balzani V.Barigelletti F.De Cola L.Flamigni L. Chem. Rev. 1994, 94: 993 - 4a 
             
            
Maestri M.Armaroli N.Balzani V.Constable EC.Cargill Thompson AMW. Inorg. Chem. 1995, 34: 2759 - 4b 
             
            
Hammarström L.Barigelletti F.Flamigni L.Indelli MT.Armaroli N.Calogero G.Guardigli M.Sour A.Collin J.-P.Sauvage J.-P. J. Phys. Chem. A 1997, 101: 9061 - 4c 
             
            
Albano G.Balzani V.Constable EC.Maestri M.Smith DR. Inorg. Chim. Acta 1998, 277: 225 - 5 
             
            
Mutai T.Cheon J.-D.Arita S.Araki K. J. Chem. Soc., Perkin Trans. 2 2001, 1045 - 6 
             
            
Goodall W.Williams JAG. Chem. Commun. 2001, 2514 - 7 
             
            
Roberto D.Tessore F.Ugo R.Bruni S.Manfredi A.Quici S. Chem. Commun. 2002, 846 - 8 
             
            
Alcock NW.Barker PR.Haider JM.Hannon MJ.Painting CL.Pikramenou Z.Plummer EA.Rissanen K.Saarenketo P. J. Chem. Soc., Dalton Trans. 2000, 1447 - 9 A comprehensive review of methods up to 1995 is provided by:  
            
Cargill Thompson AMW. Coord. Chem. Rev. 1997, 160: 1 - 10a 
             
            
Kröhnke F. Synthesis 1976, 1 - 10b 
             
            
Constable EC.Ward MD.Corr S. Inorg. Chim. Acta 1988, 141: 201 - 10c 
             
            
Frank RL.Riener EF. J. Am. Chem. Soc. 1950, 72: 4182 - 10d 
             
            
Korall P.Börje A.Norrby P.-O.Åkermark B. Acta Chem. Scand. 1997, 51: 760 - 10e 
             
            
Cave GWV.Raston CL. Chem. Commun. 2000, 2199 - 11a 
             
            
Cardenas DJ.Sauvage J.-P. Synlett 1996, 916 - 11b 
             
            
Hanan GS.Schubert US.Volkmer D.Riviere E.Lehn J.-M.Kyritsakas N.Fisher J. Can. J. Chem. 1997, 75: 169 - 11c 
             
            
Fallahpour R.-A.Neuberger M.Zehnder M. New J. Chem. 1999, 23: 53 - 11d 
             
            
Fallahpour R.-A. Eur. J. Inorg. Chem. 1998, 1205 - 12 
             
            
Goodall W.Wild K.Arm KJ.Williams JAG. J. Chem. Soc., Perkin Trans. 2 2002, 1669 - 13 During the preparation of this paper, a similar approach to synthesize 4′-p-tolyl-2,2′:6′,2′′-terpyridine was reported:  
            
Vaduvescu S.Potvin PG. Eur. J. Inorg. Chem. 2004, 1763 - 14 
             
            
Collin J.-P.Guillerez S.Sauvage J.-P.Barigelletti F.De Cola L.Flamigni L.Balzani V. Inorg. Chem. 1991, 30: 4230 - 16 
             
            
Wang J.Hanan GS.Loiseau F.Campagna S. Chem. Commun. 2004, 2068 - 17 
             
            
Yoo D.-W.Yoo S.-K.Kim C.Lee J.-K. J. Chem. Soc., Dalton Trans. 2002, 3931 - 18 
             
            
Michalec JF.Bejune SA.Cuttell DG.Summerton GC.Gertenbach JA.Field JS.Haines RJ.McMillin DR. Inorg. Chem. 2001, 40: 2193 - 19 
             
            
Husson J.Beley M.Kirsch G. Tetrahedron Lett. 2003, 44: 1767 - 20 
             
            
Persaud L.Barbiero G. Can. J. Chem. 1991, 69: 315 
References
Most of the starting aryl aldehydes were purchased from Aldrich. Aldehydes that were not commercial available were synthesized from the corresponding aryl bromides by lithiation and then formylation with dimethylformamide.