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Synthesis 2003(17): 2667-2670  
DOI: 10.1055/s-2003-42435
PAPER
© Georg Thieme Verlag Stuttgart · New York

Cross Mannich Reaction of Aldehydes; Efficient Synthesis of Substituted Pyridines

Andreas Winter, Nikolaus Risch*
Universität Paderborn, Fakultät für Naturwissenschaften, Department Chemie, Warburger Str. 100, 33098 Paderborn, Germany
Fax: +49(5251)603245; e-Mail: nr@chemie.upb.de;
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Publikationsverlauf

Received 26 September 2003
Publikationsdatum:
14. Oktober 2003 (online)

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Abstract

Symmetrically and unsymmetrically substituted pyridines were obtained in highly efficient one-pot procedures starting from α-unbranched aldehydes and iminium salts.

Key words

aldehydes - domino reactions - Mannich bases - pyridines - imines

    References

  • 1 Balasubramanian M. Keay JG. In Comprehensive Heterocyclic Chemistry II   Katritzky AR. Rees CW. Scriven EFV. Pergamon Press; Oxford: 1996. 
    Google Scholar
  • 2a Keuper R. Risch N. Flörke U. Haupt H.-J. Liebigs Ann. Org. Bioorg. Chem.  1996,  5:  705 
    Google Scholar
  • 2b Keuper R. Risch N. Liebigs Ann. Org. Bioorg. Chem.  1996,  5:  717 
    Google Scholar
  • 2c Keuper R. Risch N. Eur. J. Org. Chem.  1998,  1:  2609 
    Google Scholar
  • 2d Sielemann D. Keuper R. Risch N. J. Prakt. Chem.  1999,  341:  487 
    Google Scholar
  • 2e Sielemann D. Keuper R. Risch N. Eur. J. Org. Chem.  2000,  3:  543 
    Google Scholar
  • 3 Piper S. Dissertation   Universität Paderborn; Germany: 2003. 
    Google Scholar
  • 4 Dietrich D. Reiff H. Ziemann H. Braden R. Liebigs Ann. Chem.  1973,  111 
    Google Scholar
  • 5 Deuchert K. Hünig S. New Trends in Heterocyclic Chemistry   Elsevier; Amsterdam: 1979. 
    Google Scholar
  • 6a Komatsu M. Ohgishi H. Takamatsu S. Ohshiri Y. Agawa T. Angew. Chem., Int. Ed. Engl.  1982,  3:  213 
    Google Scholar
  • 6b Komatsu M. Takamatsu S. Uesaka M. Yamamoto S. Ohshiro Y. Agawa T. J. Org. Chem.  1984,  49:  2691 
    Google Scholar
  • 6c Vijn RJ. Arts HJ. Green R. Caselijns AM. Synthesis  1994,  573 
    Google Scholar
  • 6d Soldatenkov A. Fedorov VO. Chandra R. Polosin VM. Mikaya AI. Prostakov NS. J. Org. Chem. USSR Engl. Transl.  1980,  16:  473 
    Google Scholar
  • 7 Sielemann D. Dissertation   Universität Paderborn; Germany: 2000. 
    Google Scholar
  • 8 Böhme H. Auterhoff G. Chem. Ber.  1971,  104:  2013 
    CrossrefGoogle Scholar
  • 9 Kinast G. Tietze LF. Angew. Chem.  1976,  88:  261 
    CrossrefGoogle Scholar
  • 10a Jeyashri B. Balasubrahmanyam SN. Indian J. Chem. Sect. B  1985,  25:  341 
    CrossrefGoogle Scholar
  • 10b Kim BH. Jeon I. Han TH. Park HJ. Jun YM. J. Chem. Soc., Perkin Trans. 1  2001,  17:  2035 
    CrossrefGoogle Scholar
  • 10c Kagabu S. Ando C. Ando J. J. Chem. Soc., Perkin Trans. 1  1994,  6:  739 
    CrossrefGoogle Scholar
  • 10d Katritzky AR. Mazurkiewicz R. Stevens CV. Godeev MF. J. Org. Chem.  1994,  59:  2740 
    CrossrefGoogle Scholar