Synthesis 2011(9): 1465-1471  
DOI: 10.1055/s-0030-1259970
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Reaction of Ethyl 5-Acetyl-3,4-dihydropyridine-1(2H)-carboxylate with 1,3-N,N-Bis-nucleophiles: A Facile Access to Novel Pyrimidine Derivatives

Nazar B. Maximova,b, Pavel K. Mykhailiuk*a,b, Andrei I. Kiselb, Zoia V. Voitenkob, Andrey A. Tolmacheva,b
a Enamine Ltd., Alexandra Matrosova Street 23, 01103 Kiev, Ukraine
b Department of Chemistry, Kiev National Taras Shevchenko University, Volodymyrska Street 64, 01033 Kiev, Ukraine
Fax: +380(44)2351273; e-Mail: pavel.mykhailiuk@gmail.com;
Further Information

Publication History

Received 27 January 2011
Publication Date:
24 March 2011 (online)

Abstract

Reaction of ethyl 5-acetyl-3,4-dihydropyridine-1(2H)-carboxylate with diverse 1,3-N,N-bis-nucleophiles results in the regioselective formation of the correspondingly substituted pyrimidines in good yields.

    References

  • 1 Quin LD. Pinion DO. J. Org. Chem.  1970,  35:  3130 
  • 2 Maximov NB. Mykhailiuk PK. Golovach SM. Tverdokhlebov AV. Voitenko ZV. Tolmachev AA. Synthesis  2010,  1781 
  • 3 Wenkert E. Dave KG. Haglid F. Lewis RG. Oishi T. Stevens RV. Terashima M. J. Org. Chem.  1968,  33:  747 
  • For similar recyclizations of cyclic 1,3-bis-electrophiles into pyrimidines, see:
  • 4a Kawase M. Hirabayashi M. Saito S. Yamamoto K. Tetrahedron Lett.  1999,  40:  2541 
  • 4b Zanatta N. Fagundes MB. Ellensohn R. Marques M. Bonacorso HG. Martins MAP. J. Heterocycl. Chem.  1998,  35:  451 
  • 4c Zanatta N. Cortelini MFM. Carpes MJS. Bonacorso HG. Martins MAP. J. Heterocycl. Chem.  1997,  34:  509 
  • 4d Effenberger F. Barthelmess I. J. Heterocycl. Chem.  1995,  32:  599 
  • 4e Rossi E. Abbiati G. Pini E. Synlett  1999,  1265 
  • 4f Sagar R. Kim M.-J. Park SB. Tetrahedron Lett.  2008,  49:  5080 
  • 4g Kotljarov A. Irgashev RA. Sosnovskikh VY. Iaroshenko VO. Sevenard DV. Synthesis  2009,  3233