H. Namazi, Y. Mirzaei, H. Azamat
Sep 1, 2001
Citations
0
Influential Citations
23
Citations
Journal
Journal of Heterocyclic Chemistry
Abstract
The compounds 5-ethoxycarbonyl-1,6-dimethyl-4-(3-nitrophenyl)-3,4-dihydropyrimidin-2(lH)-one (5) and 5-ethoxycarbonyl-1-phenyl-6-methyl-4-(3-nitrophenyl)-3,4-dihydropyrimidin-2(lH)-one (1) were prepared by the Biginelli condensation method and they converted to eight N-3 substituted dihydropyrimidines using NaH and various electrophiles (ClCO2Et, TsCl, Ac2O, AcCl and PhCOCl). Compound (1) was mono-brominated at the C6-methyl group using bromine solution. Reaction of the bromo derivative with amino nucleophiles such as methyl amine and cyclohexyl amine produced two pyrrolo-pyrimidine derivatives. All the compounds except 5-ethoxycarbonyl-1-phenyl-6-methyl-4-(3-nitrophenyl)-3,4-dihydropyrimidin-2(lH)-one (4) were purified by recrystallization methods. The structure of all the new compounds was confirmed using FT-ir,1H nmr, 13C nmr spectral and elemental analyses methods.