Synthesis 2010(11): 1781-1792  
DOI: 10.1055/s-0029-1219760
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Regioselective Reaction of Ethyl 5-Acetyl-3,4-dihydropyridine-1(2H)-carboxylate with Hydrazines: A Facile Approach to New Pyrazole Derivatives

Nazar B. Maximova,b, Pavel K. Mykhailiuk*a,b, Sergey M. Golovacha, Anton V. Tverdokhlebova,b, Zoya V. Voitenkob, Andrey A. Tolmacheva,b
a Enamine Ltd., Alexandra Matrosova Street 23, Kiev 01103, Ukraine
b Department of Chemistry, Kiev National Taras Shevchenko University, Volodymyrska Street 64, Kiev 01033, Ukraine
Fax: +380(44)2351273; e-Mail: Pashamk@gmx.de;
Further Information

Publication History

Received 26 February 2010
Publication Date:
06 April 2010 (eFirst)

  Buy Article Permissions and Reprints All articles of this category

Abstract

The reaction of ethyl 5-acetyl-3,4-dihydropyridine-1(2H)-carboxylate with diverse aliphatic as well as aromatic monosubstituted hydrazines resulted in the regioselective formation of N-substituted 3-methylpyrazoles.

Key words

pyrazole - hydrazine - tetrahydropyridine - regioselectivity

    References

  • 1 Elguero J. Goya P. Jagerovic N. Silva AMS. Targets Heterocycl. Syst.  2002,  6:  52 ; and references therein
  • 2a Singer RA. Caron S. McDermott RE. Arpin P. Do NM. Synthesis  2003,  1727 
  • 2b Singer RA. Dore M. Sieser JE. Berliner MA. Tetrahedron Lett.  2006,  47:  3727 
  • 3a Quin LD. Pinion DO. J. Org. Chem.  1970,  35:  3134 
  • 3b Bajnati A. Huber-Habart M. Bull. Soc. Chim. Fr.  1988,  3:  540 
  • 3c Quan PM. Quin LD. J. Org. Chem.  1966,  31:  2487 
  • 3d Wenkert E. Moeller P. Pietre S. J. Am. Chem. Soc.  1988,  110:  7188 
  • 3e Wenkert E. Hudlicky T. J. Org. Chem.  1968,  33:  747 
  • 3f Quin LD. Pinion DO. J. Org. Chem.  1970,  35:  3130 
  • 3g Wenkert E. Dave K. Haglid F. Lewis R. Oishi T. Stevens R. Terashima M. J. Org. Chem.  1968,  33:  747 
  • 3h Lei A. Chan M. He M. Zhang X. Eur. J. Org. Chem.  2006,  19:  4343 
  • 4a Okada E. Heterocycles  1992,  34:  791 
  • 4b Menozzi G. Mosti L. Schenone P. J. Heterocycl. Chem.  1987,  24:  1669 
  • 4c Dehayes C. Chabannet M. Gelin S. Synthesis  1982,  1088 
  • 4d Dehayes C. Chabannet M. Gelin S. J. Heterocycl. Chem.  1984,  21:  301 
  • 4e Golovinsky EV. Spassova MK. Zakharieva RD. Z. Chem.  1980,  20:  95 
  • 4f Bajnati A. Bull. Soc. Chim. Fr.  1988,  3:  540