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Synthesis 2011(18): 3006-3014  
DOI: 10.1055/s-0030-1261033
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Effective Suzuki-Miyaura Arylation and Sonogashira Aryl Alkynylation on N-Heteroaromatic Cations: Synthesis of Substituted Pyridine-Fused Cationic Heterocycles

Rupankar Paira, Krishnendu B. Sahu, Shyamal Mondal, Arindam Maity, Abhijit Hazra, Subhendu Naskar, Pritam Saha, E. Padmanaban, Sukdeb Banerjee, Nirup B. Mondal*
Department of Chemistry, Indian Institute of Chemical Biology, Council of Scientific and Industrial Research, 4 Raja S.C. Mullick Road, Jadavpur, Kolkata-700032, India
Fax: +91(33)24735197; e-Mail: nirup@iicb.res.in;
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Publication History

Received 15 June 2011
Publication Date:
05 August 2011 (online)

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Abstract

Suzuki-Miyaura and Sonogashira cross-coupling reactions were efficiently employed for the syntheses of aryl, biaryl, and aryl alkynyl substituted polycyclic tetrahydropyrimidinium, di­azepanium, and diazocanium derivatives with moderate-to-high yields. Appropriately functionalized pyridinium templates for these syntheses were obtained under microwave irradiation, using basic alumina as the solid support.

Key words

Suzuki-Miyaura - Sonogashira - cross-coupling - fused rings - diazepanium - diazocanium

    References

  • 1 Brana MF. Cacho M. Gradillas A. de Pascual-Teresa B. Ramos A. Curr. Pharm. Des.  2001,  7:  1745 
    CrossrefSearch in Google Scholar
  • 2 Galietta LJV. Springsteel MF. Eda M. Niedzinski EJ. By K. Haddadin MJ. Kurth MJ. Nantz MH. Verkman AS. J. Biol. Chem.  2001,  276:  19723 
    CrossrefSearch in Google Scholar
  • 3 Martínez V. Burgos C. Alvarez-Builla J. Fernández G. Domingo A. García-Nieto R. Gago F. Manzanares I. Cuevas C. Vaquero JJ. J. Med. Chem.  2004,  47:  1136 
    CrossrefSearch in Google Scholar
  • 4a Howarth J. Hanlon K. Tetrahedron Lett.  2001,  42:  751 
    Search in Google Scholar
  • 4b Howarth J. Hanlon K. Bioorg. Med. Chem. Lett.  2003,  13:  2017 
    Search in Google Scholar
  • 5a García D. Cuadro AM. Alvarez-Builla J. Vaquero JJ. Org. Lett.  2004,  6:  4175 
    Search in Google Scholar
  • 5b Lambert C. Gaschler W. Nöll G. Weber M. Schmälzlin E. Bräuchle C. Meerholz K. J. Chem. Soc., Perkin Trans. 2  2001,  964 
  • 5c Barchín BM. Valenciano J. Cuadro AM. Alvarez-Builla J. Vaquero JJ. Org. Lett.  1999,  1:  545 
    Search in Google Scholar
  • 5d Reyes MJ. Izquierdo ML. Alvarez-Builla J. Tetrahedron Lett.  2004,  45:  8713 
    Search in Google Scholar
  • 5e Córdoba M. Izquierdo ML. Alvarez-Builla J. Tetrahedron Lett.  2011,  52:  1738 
    Search in Google Scholar
  • 6a Bringmann G. Gunther C. Ochse M. Schupp O. Tasler S. In Progress in the Chemistry of Organic Natural Products   Vol. 82:  Herz W. Falk H. Kirby GW. Moore RE. Tamm C. Springer; Vienna: 2001.  p.1-249  
    Search in Google Scholar
  • 6b Bringmann G. Feineis D. Acta Chim. Ther.  2000,  26:  151 
    Search in Google Scholar
  • 6c Bringmann G. In Guidelines and Issues for the Discovery and Drug Development against Tropical Diseases   Vial H. Fairlamb A. Ridley R. World Health Organisation; Geneva: 2003.  p.145-152  
  • 7a Miyaura N. Yamada K. Suzuki A. Tetrahedron Lett.  1979,  3437 
  • 7b Miyaura N. Suzuki A. Chem. Rev.  1995,  95:  2457 
    Search in Google Scholar
  • 7c Suzuki A. J. Organomet. Chem.  1999,  576:  147 
    Search in Google Scholar
  • 7d Suzuki A. J. Organomet. Chem.  2002,  653:  83 
    Search in Google Scholar
  • 7e Kotha S. Lahiri K. Kashinath D. Tetrahedron  2002,  58:  9633 
    Search in Google Scholar
  • 7f Miyaura N. In Metal-Catalyzed Cross-Coupling Reactions   2nd ed., Vol. 1:  de Meijere A. Diederich F. Wiley-VCH; Weinheim: 2004.  p.41-124  
    Search in Google Scholar
  • 8a De Clercq E. Descamps J. Balzarini J. Giziewicz J. Barr PJ. Robins MJ. J. Med. Chem.  1983,  26:  661 
    Search in Google Scholar
  • 8b Fairlamb IJS. Marrison LR. Dickinson JM. Lu FJ. Schmidt JP. Bioorg. Med. Chem.  2004,  12:  4285 
    Search in Google Scholar
  • 9a Sonogashira K. Tohda Y. Hagihara N. Tetrahedron Lett.  1975,  4467 
  • 9b Sonogashira K. Yatake T. Tohda Y. Takahashi S. Hagihara N. Chem. Commun.  1977,  291 
  • 10a Saha P. Naskar S. Paira P. Hazra A. Sahu KB. Paira R. Banerjee S. Mondal NB. Green Chem.  2009,  7:  931 
    Search in Google Scholar
  • 10b Sahu KB. Hazra A. Paira P. Saha P. Naskar S. Paira R. Banerjee S. Sahu NP. Mondal NB. Luger P. Weber M. Tetrahedron  2009,  65:  6941 
    Search in Google Scholar
  • 10c Paira P. Paira R. Hazra A. Sahu KB. Naskar S. Saha P. Mondal S. Maity A. Banerjee S. Mondal NB. Tetrahedron Lett.  2009,  50:  5505 
    Search in Google Scholar
  • 10d Paira R. Maity A. Naskar S. Mondal S. Paira P. Hazra A. Sahu KB. Saha P. Banerjee S. Mondal NB. Synthesis  2010,  3520 
  • 11 Paira R. Maity A. Mondal S. Naskar S. Sahu KB. Saha P. Hazra A. Padmanaban E. Banerjee S. Mondal NB. Tetrahedron Lett.  2011,  52:  1653 
    CrossrefSearch in Google Scholar
  • 12 Cheng D. Croft l. Abdi M. Lightfoot A. Gallagher T. Org. Lett.  2007,  9:  5175 
    Search in Google Scholar