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Synthesis 2011(9): 1465-1471
DOI: 10.1055/s-0030-1259970
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
Further Information
Received
27 January 2011
Publication Date:
24 March 2011 (online)
Publication History
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.
Key words
pyrimidines - amidines - amino heterocycles - tetrahydropyridine
- 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