Download PDF
Synthesis 2010(24): 4228-4234  
DOI: 10.1055/s-0030-1258274
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Simple Selective Synthesis of 2,4- and 2,6-Diarylpyridines through Metal-Free Cyclocondensation of Aromatic Ketones with Ammonium Acetate

Jin Liu, Chuanxin Wang, Liansheng Wu, Fen Liang, Guosheng Huang*
State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. of China
Fax: +86(931)8912582; e-Mail: hgs2368@163.com;
Further Information

Publication History

Received 10 August 2010
Publication Date:
28 September 2010 (online)

    Permissions and Reprints All articles of this category

Abstract

A simple and selective one-pot synthesis of 2,4- and 2,6-diarylpyridines through the cyclocondensation reaction of aromatic ketones with ammonium acetate has been developed. The procedure is metal-free, convenient, and efficient, and the substrates are readily available.

Key words

diarylpyridines - selective - cyclocondensation - aromatic ketones - ammonium acetate

    References

  • 1a Roth HJ. Kleemann A. Drug Synthesis in Pharmaceutical Chemistry   Vol. 1:  John Wiley and Sons; New York: 1988. 
    Google Scholar
  • 1b Michael JP. Nat. Prod. Rep.  2005,  22:  627 
    Google Scholar
  • 1c Nicolaou KC. Bulger PG. Sarlah D. Angew. Chem. Int. Ed.  2005,  44:  4442 
    Google Scholar
  • 2a Kawamura S. Hamada T. Sato R. J. Agric. Food Chem.  1991,  39:  2279 
    Google Scholar
  • 2b Matolcsy G. Pesticide Chemistry   Elsevier Scientific; Amsterdam: 1998.  p.427-430  
    Google Scholar
  • 3a Surry DS. Buchwald SL. Angew. Chem. Int. Ed.  2008,  47:  6338 
    Google Scholar
  • 3b Cabeza JA. del Río I. Pérez-Carreňo E. Sánchez-Vega GM. Vázquez-García D. Angew. Chem. Int. Ed.  2009,  48:  555 
    Google Scholar
  • 4a Togni A. Venanzi LM. Angew. Chem. Int. Ed.  1994,  33:  497 
    Google Scholar
  • 4b Fache F. Schulz E. Tommasino ML. Lemaire M. Chem. Rev.  2000,  100:  2159 
    Google Scholar
  • 5a Vaz AD. Coon MJ. Peegel H. Meenon KM. Drug Metab. Dispos.  1992,  20:  108 
    Google Scholar
  • 5b Selvaraj M. Lee TG. Microporous Mesoporous Mater.  2005,  85:  52 
    Google Scholar
  • 6a Bouras A. Boggetto N. Benatalah Z. de Rosny E. Sicsic S. Rebound-Ravaux M. J. Med. Chem.  1999,  42:  957 
    Google Scholar
  • 6b Matrunola CA. Moody CJ. Robertson AAB. Warne MR. Tetrahedron Lett.  2003,  44:  1627 
    Google Scholar
  • 7a Zhao LX. Sherchan J. Park JK. Jahng Y. Jeong BS. Jeong TC. Lee CS. Lee ES. Arch. Pharmacal. Res.  2006,  29:  1091 
    Google Scholar
  • 7b Basnet A. Thapa P. Karki R. Na Y. Jahng Y. Jeong BS. Jeong TC. Lee CS. Lee ES. Bioorg. Med. Chem.  2007,  15:  4351 
    Google Scholar
  • 8a Yamada S. Coord. Chem. Rev.  1999,  190:  537 
    Google Scholar
  • 8b Kozhevnikov VN. Kozhevnikov DN. Nikitina TV. Rusinov VL. Chupakhin OL. Zabel M. Konig B. J. Org. Chem.  2003,  68:  2882 
    Google Scholar
  • 9 Lin C. Kagan CR. J. Am. Chem. Soc.  2003,  125:  336 
    CrossrefGoogle Scholar
  • 10 Soto E. MacDonald JC. Cooper CGF. McGimpsey WG. J. Am. Chem. Soc.  2003,  125:  2838 
    CrossrefGoogle Scholar
  • 11a Sweetman BA. Müller-Bunz H. Guiry PJ. Tetrahedron Lett.  2005,  46:  4643 
    Google Scholar
  • 11b Durola F. Sauvage JP. Wenger OS. Chem. Commun.  2006,  171 
    Google Scholar
  • 12 Recent review of de novo methods for pyridine synthesis: Henry GD. Tetrahedron  2004,  60:  6043 
    CrossrefGoogle Scholar
  • For selected recent examples on the transition-metal-catalyzed synthesis of substituted pyridines:
  • 13a McCormick MM. Duong HA. Zuo G. Louie J. J. Am. Chem. Soc.  2005,  127:  5030 
    Google Scholar
  • 13b Chang H.-T. Jeganmohan M. Cheng C.-H. Org. Lett.  2007,  9:  505 
    Google Scholar
  • 13c Kase K. Goswami A. Ohtaki K. Tanabe E. Saino N. Okamoto S. Org. Lett.  2007,  9:  931 
    Google Scholar
  • 13d Colby DA. Bergman RG. Ellman JA. J. Am. Chem. Soc.  2008,  130:  3645 
    Google Scholar
  • 13e Parthasarathy K. Jeganmohan M. Cheng C.-H. Org. Lett.  2008,  10:  325 
    Google Scholar
  • For selected recent examples on the synthesis of substituted pyridines via multicomponent reactions:
  • 14a Senaiar RS. Young DD. Deiter A. Chem. Commun.  2006,  1313 
    Google Scholar
  • 14b Evdokimov N. Magedov IV. Kireev AS. Kornienko A. Org. Lett.  2006,  8:  899 
    Google Scholar
  • 14c Dash J. Lechel T. Reissig H.-U. Org. Lett.  2007,  9:  5541 
    Google Scholar
  • 14d Ranu BC. Jana R. Sowmiah S. J. Org. Chem.  2007,  72:  3152 
    Google Scholar
  • 14e Zhu S.-L. Ji S.-J. Su X.-M. Sun C. Liu Y. Tetrahedron Lett.  2008,  49:  1777 
    Google Scholar
  • 14f Sasada T. Sakai N. Konakahara T. J. Org. Chem.  2008,  73:  6905 
    Google Scholar
  • For selected recent examples on the synthesis of substituted pyridines via using ammonium acetate as the nitrogen source:
  • 15a Ladouceur GH. Cook JH. Doherty EM. Schoen WR. MacDougall ML. Livingston JN. Bioorg. Med. Chem. Lett.  2002,  12:  461 
    Google Scholar
  • 15b Rodriguez H. Suarez M. Perez R. Petit A. Loupy A. Tetrahedron Lett.  2003,  44:  3709 
    Google Scholar
  • 15c Bowman MD. Jacobson MM. Pujanauski BG. Blackwell HE. Tetrahedron  2006,  62:  4715 
    Google Scholar
  • 15d Liéby-Muller F. Allais C. Constantieux T. Rodriguez J. Chem. Commun.  2008,  4207 
    Google Scholar
  • For selected recent examples on the synthesis of diarylpyridines via vapor-phase cyclization of acetophenone, formaldehyde and ammonia:
  • 16a Ratnamala A. Subrahmanyam M. Kumari VD. Appl. Catal., A  2004,  264:  219 
    Google Scholar
  • 16b Selvaraj M. Lee TG. Microporous Mesoporous Mater.  2005,  85:  52 
    Google Scholar
  • For selected recent examples on the synthesis of diarylpyridines via arylation of the pyridine nucleus with organometallic reagents:
  • 17a Munoz B. Chixu C. McDonald IA. Biotechnol. Bioeng.  2000,  71:  78 
    Google Scholar
  • 17b Littke AF. Dai C. Fu GC. J. Am. Chem. Soc.  2000,  122:  4020 
    Google Scholar
  • 17c Handy ST. Wilson T. Muth A. J. Org. Chem.  2007,  72:  8496 
    Google Scholar
  • For selected recent examples on the synthesis of diarylpyridines via palladium-catalyzed direct arylation of pyridine N-oxides:
  • 18a Campeau L.-C. Rousseaux S. Fagnou K. J. Am. Chem. Soc.  2005,  127:  18020 
    Google Scholar
  • 18b Andersson H. Almqvist F. Olsson R. Org. Lett.  2007,  9:  1335 
    Google Scholar
  • 18c Schipper DJ. El-Salfiti M. Whipp CJ. Fagnou K. Tetrahedron  2009,  65:  4977 
    Google Scholar
  • 19 Eliel EL. McBride RT. Kaufmann St. J. Am. Chem. Soc.  1953,  75:  4291 
    CrossrefGoogle Scholar
  • 20a Engler C. Heine H. Ber. Dtsch. Chem. Ges.  1873,  6:  638 
    Google Scholar
  • 20b Reihm P. Justus Liebigs Ann. Chem.  1887,  238:  1 
    Google Scholar
  • 20c Elderfield RC. King TP. J. Am. Chem. Soc.  1954,  76:  5437 
    Google Scholar
  • 20d Sargent LJ. J. Org. Chem.  1956,  21:  1286 
    Google Scholar
  • 20e Adib M. Tahermansouri H. Koloogani SA. Mohammadi B. Bijanzadeh HR. Tetrahedron Lett.  2006,  47:  5957 
    Google Scholar
  • 20f Wang LF. Zhang HY. Kong L. Chen ZW. Shi JG. Helv. Chim. Acta  2004,  87:  1515 
    Google Scholar