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Synthesis 2011(2): 210-212  
DOI: 10.1055/s-0030-1258342
SHORTPAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Diisothiocyanato-Functionalized 2,2′-Bipyridines

Christopher Kremer, Arne Lützen*
University of Bonn, Kekulé-Institute of Organic Chemistry and Biochemistry, Gerhard-Domagk-Str. 1, 53121 Bonn, Germany
Fax: +49(228)739608; e-Mail: arne.luetzen@uni-bonn.de;
Further Information

Publication History

Received 15 October 2010
Publication Date:
26 November 2010 (online)

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Abstract

Three new diisothiocyanato-functionalized 2,2′-bipyridines have been synthesized in four consecutive steps. Starting from 4-amino-2-chloro- and 2-amino-6-bromopyridine, respectively, we first prepared the corresponding diamino-2,2′-bipyridines via homo- or Negishi cross-coupling reactions which were subsequently reacted with thiophosgene.

Key words

bipyridine - isothiocyanates - amines - thiophosgene - cross-coupling reactions

    References

  • 1 Smith AP. Fraser CL. In Comprehensive Coordination Chemistry II   Vol. 1:  McCleverty JA. Meyer TJ. Elsevier; Oxford: 2004.  p.1 
    Google Scholar
  • 2 Kaes C. Katz A. Hosseini MW. Chem. Rev.  2000,  100:  3553 
    CrossrefGoogle Scholar
  • 3 Schalley CA. Lützen A. Albrecht M. Chem. Eur. J.  2004,  10:  1072 
    CrossrefGoogle Scholar
  • 4 Hannon MJ. Childs LJ. Supramol. Chem.  2006,  16:  7 
    Google Scholar
  • 5 Photochemistry and Photophysics of Coordination Compounds I + II, In Topics in Current Chemistry   Vols. 280 and 281:  Balzani V. Campagna S. Springer Verlag; Berlin: 2007. 
    Google Scholar
  • Recent reviews with focus on chiral 2,2′-bipyridines:
  • 6a Malkov AV. Kočovs P. Curr. Org. Chem.  2003,  7:  1737 
    Google Scholar
  • 6b Kwong H.-L. Yeung H.-L. Yeung C.-T. Lee W.-S. Lee C.-S. Wong W.-L. Coord. Chem. Rev.  2007,  251:  2188 
    Google Scholar
  • 7a Trecourt F. Gervais B. Mongin O. Le Gal C. Mongin F. Quéguiner G. J. Org. Chem.  1998,  63:  2892 
    Google Scholar
  • 7b Mongin F. Trecourt F. Gervais B. Mongin O. Quéguiner G. J. Org. Chem.  2002,  67:  3272 
    Google Scholar
  • 7c Du W. Tetrahedron  2003,  59:  8649 
    Google Scholar
  • 7d Bringmann G. Reichert Y. Kane VV. Tetrahedron  2004,  60:  3539 
    Google Scholar
  • 7e Sammakia T. Stangeland EL. Whitcomb MC. In Strategies and Tactics in Organic Synthesis   Vol. 6:  Harmata M. Elsevier; New York: 2005.  p.415 
    Google Scholar
  • 8a Newkome GR. Patri AK. Holder E. Schubert US. Eur. J. Org. Chem.  2004,  235 
    Google Scholar
  • 8b Hapke M. Brand L. Lützen A. Chem. Soc. Rev.  2008,  37:  2782 
    Google Scholar
  • 9a Lützen A. Hapke M. Griep-Raming J. Haase D. Saak W. Angew. Chem. Int. Ed.  2002,  41:  2086 ; Angew. Chem. 2002, 114, 2190
    Google Scholar
  • 9b Kiehne U. Weilandt T. Lützen A. Org. Lett.  2007,  9:  1283 
    Google Scholar
  • 9c Kiehne U. Lützen A. Org. Lett.  2007,  9:  5333 
    Google Scholar
  • 9d Kiehne U. Weilandt T. Lützen A. Eur. J. Org. Chem.  2008,  2056 
    Google Scholar
  • 9e Bunzen J. Bruhn T. Bringmann G. Lützen A. J. Am. Chem. Soc.  2009,  131:  3621 
    Google Scholar
  • 9f Bunzen J. Hovorka R. Lützen A. J. Org. Chem.  2009,  74:  5228 
    Google Scholar
  • 9g Bunzen J. Hapke M. Lützen A. Eur. J. Org. Chem.  2009,  3885 
    Google Scholar
  • 9h Bunzen J. Kiehne U. Benkhäuser-Schunk C. Lützen A. Org. Lett.  2009,  11:  4786 
    Google Scholar
  • 9i Dalla Favera N. Kiehne U. Bunzen J. Hytteballe S. Lützen A. Piguet C. Angew. Chem. Int. Ed.  2010,  49:  125 ; Angew. Chem. 2010, 122, 129
    Google Scholar
  • 9j Piehler T. Lützen A. Z. Naturforsch. B: Chem. Sci.  2010,  65:  329 
    Google Scholar
  • 10a Lützen A. Haß O. Bruhn T. Tetrahedron Lett.  2002,  43:  1807 
    Google Scholar
  • 10b Zahn S. Reckien W. Staats H. Matthey J. Lützen A. Kirchner B. Chem. Eur. J.  2009,  15:  2572 
    Google Scholar
  • 10c Staats H. Eggers F. Haß O. Fahrenkrug F. Matthey J. Lüning U. Lützen A. Eur. J. Org. Chem.  2009,  4777 
    Google Scholar
  • 10d Staats H. Lützen A. Beilstein J. Org. Chem.  2010,  6:  No. 10 ; http://www.beilstein-journals.org/bjoc/home/home.htm
    Google Scholar
  • 11 Gunnlaugsson T. Glynn M. Tocci (née Hussey) GM. Kruger PE. Pfeffer FM. Coord. Chem. Rev.  2006,  250:  3094 
    CrossrefGoogle Scholar
  • 12a Connon SJ. Chem. Eur. J.  2006,  12:  5418 
    Google Scholar
  • 12b Miyabe H. Takemoto Y. Bull. Chem. Soc. Jpn.  2008,  81:  785 
    Google Scholar
  • 12c Zhang Z. Schreiner PR. Chem. Soc. Rev.  2009,  38:  1187 
    Google Scholar
  • 12d Takemoto Y. Chem. Pharm. Bull.  2010,  58:  593 
    Google Scholar
  • 13 Rodríguez-Fernández E. Manzano JL. Benito JJ. Hermosa R. Monte E. Criado JJ. J. Inorg. Biochem.  2005,  99:  1558 
    CrossrefGoogle Scholar
  • 14 Braverman S. Cherkinsky M. Birsa ML. Science of Synthesis   Vol. 18:  Knight J. Georg Thieme Verlag; Stuttgart: 2005.  p.65 
    Google Scholar
  • 15 Janiak C. Deblon S. Wu H.-P. Synth. Commun.  1999,  29:  3341 
    CrossrefGoogle Scholar
  • 16 Hapke M. Staats H. Wallmann I. Lützen A. Synthesis  2007,  2711 
    Article in Thieme ConnectGoogle Scholar
  • 17 Munch H. Hansen JS. Pittelkow M. Christensen JB. Boas U. Tetrahedron Lett.  2008,  49:  3117 
    CrossrefGoogle Scholar
  • 18 Lützen A. Hapke M. Staats H. Bunzen J. Eur. J. Org. Chem.  2003,  3948 
    CrossrefGoogle Scholar
  • 19 Kiehne U. Bunzen J. Staats H. Lützen A. Synthesis  2007,  1061 
    Article in Thieme ConnectGoogle Scholar