Synthesis and Characterization of Novel Biginelli Dihydropyrimidinone Derivatives Containing Imidazole Moiety

Abstract

Enaminone, (2E)-1-[4-(1H-imidazol-1-yl) phenyl]-4-methylpent-2-en-1-one (II) was synthesized by refluxing 1-[4-(1H-imidazol-1-yl) phenyl] ethan-1-one (I) with dimethylforamide dimethylacetal (DMF–DMA) under solvent-free condition for 12 hours. Finally, the dihydropyrimidinone derivatives containing imidazole moiety (1–15) were obtained by reacting enaminone, (2E)-1-[4-(1H-imidazol-1-yl) phenyl]-4-methylpent-2-en-1-one (II) with urea and different substituted benzaldehydes in the presence of glacial acetic acid. Dihydropyrimidinone derivatives containing imidazole moiety were synthesized in excellent yield by means of a simple and efficient method. All the compounds were confirmed by elemental analysis. The structures of all the compounds were confirmed by modern spectroscopic methods.

Facile synthesis and anticancer activity of novel dihydropyrimidinone derivatives

“…Two NH protons of dihydropyrimidinones were observed as exchangeable protons at δ 9.1-9.2 ppm and δ 9.8-10.2 ppm. The H-4 protons of dihydropyrimidinone were observed at δ 5.3-5.6 ppm 25 . In GC/MS analysis, all the synthesized compounds present molecular ion peaks according to their molecular weights (Fig.…”

PROSPECTS FOR THE CHEMISTRY OF IMIDAZOLE DERIVATIVES (Review)

“…After heating the mixture, 2-phenyl-4-methoxycarbonylmethylene-1(3H)-imidazol-5-one (40) was formed. The latter reacts with hydrazine hydrate in methanol to yield 2phenyl-4-hydrazinecarbonylmethylene-1(3H)-imidazol-5-one (41). Carbon disulfide and potassium hydroxide were added to 2-phenyl-4hydrazinecarbonylmethylene-1(3H)-imidazol-5-one (41) in ethanol to synthesize N-[(2-phenyl-1(3H)-imidazol-5-on-4-ylidene)acetyl]hydrazine potassium carbodithioate (42).…”

“…The latter reacts with hydrazine hydrate in methanol to yield 2phenyl-4-hydrazinecarbonylmethylene-1(3H)-imidazol-5-one (41). Carbon disulfide and potassium hydroxide were added to 2-phenyl-4hydrazinecarbonylmethylene-1(3H)-imidazol-5-one (41) in ethanol to synthesize N-[(2-phenyl-1(3H)-imidazol-5-on-4-ylidene)acetyl]hydrazine potassium carbodithioate (42). Following this, carbodithioate without further purification, and hydrazine hydrate in water refluxed while stirring to furnish 4-(4-amino-5thioxo-4,5-dihydro-1H-1,2,4-triazol-3-ylmethylen)-2-phenyl-1(3H)-imidazol-5one ( 43).…”

“…Bhat M.A. et al [41] synthesized imidazole derivatives of dihydropyrimidinone. (2E)-1-[4-(1H-Imidazol-1-yl)phenyl]-4-methylpent-2-en-1one (48) was synthesized by refluxing 1-[4-(1H-imidazol-1-yl)phenyl]ethan-1one (47) with dimethylformamide-dimethylacetal (DMF-DMA) for 12 h without a solvent.…”