Synthesis and Characterization of Some 1,4-Dihydropyridine Derivatives Containing Dichlorothiazolyl Substituents
K.M. TAGHI-GANJI, SH. GHODSI†, E. ALIPOUR*, M. AMINI‡ , M. HOSSEINI and A. SHAFIEE‡

Faculty of Chemistry, Islamic Azad University, North Tehran - Branch, Tehran, Iran
Tel: (98)(212)2803801; Fax: (98)(212)2222512; E-mail: ej_alipour@yahoo.com

Abstract

4-Substituted heterocycles or aryl dihydropyridines (DHP) with various C3, C5 diesters have calcium channel antagonist activity. In this paper a group of dialkyl, dicycloalkyl and diaryl ester analogues of nifedipine, in which the ortho nitro phenyl group at position 4 is replaced by 2,4-dichloro-5-thiazolyl substituent is presented. The Hantzsch condensation of alkyl acetoacetate (3) and ammonium acetate with 2,4-dichloro-1,3-thiazole-5-carboxaldehyde (2) offered symmetrical dialkyl 1,4-dihydro-2,6-dimethyl-4-(2,4-dichloro-1,3-thiazolyl)-3,5-pyridinedicarboxylates. Whereas condensation of 2 with 3 and 5 gave the asymmetrical dialkyl esters.
Keywords

e, Dihydropyridines, Dichlorothiazoles,Thiazole synthesis, Nifedipine analogues.
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  • Asian J. Chem. /
  •  2007 /
  •  19(4) /
  •  pp 2521-2526