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Synthesis of New Dihydropyrimidine 2-(lH)-one Compounds | ||
| Al-Mustansiriyah Journal of Science | ||
| Article 1, Volume 20, Issue 3, 2009, Pages 53-65 | ||
| Author | ||
| Redha I. H. Al-BAyati | ||
| Abstract | ||
| In this work, ethyI-4-(4-chloro phenyl)-6-methyl-2-oxo-1,2.3-4-tetrahydro pyrimidine-5-carboxylate (1) was prepared from condensation of ethyl acetoacetate with 4-chloro benzaldehyde and urea in the presence of LaCl3.7H2O and then hydrolyzed to the corresponding acid (2) by using sodium hydroxide. Reaction of acid (2) with excess SOCl2 was yielded the acid chloride (3), which upon reactions with propargyl alcohol and dicyclohexylamine afforded the corresponding prop-2-ynyl carboxylate derivatives (4) carboxamide (5) respectively. On the other hand, reaction of (1) with thiosemicarbazide in dry toluene gave acyl thiosemicarbazide (6) which upon ring closure with cone. H2SO4 and NaOH afforded 1,3,4-thiadiazole (7) and 1,2,4-triazole (8) moieties derivatives respectively. Subsequent reaction of (8) with NH2NH2 gave hydrazino-4H-1,2,4-triazole moiety derivative (9). Moreover, bromonation of (1) with NBS afforded bromomethyl derivative (10) and used for the synthesis of series of dihydropyrimidine derivatives (11-15) through nucleophilic substitution reaction. The synthesized compounds were verified by their 1R and UV Special data. | ||
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