A One-Pot Biginelli Synthesis and Characterization of Novel Dihydropyrimidinone Derivatives Containing Piperazine/Morpholine Moiety

et al. 2019

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.

Section: Resultsmentioning

confidence: 99%

Synthesis and Characterization of Novel Biginelli Dihydropyrimidinone Derivatives Containing Imidazole Moiety

et al. 2019

“…Enaminone derivatives (1-11) were used as a starting material for the synthesis of various pyrazole derivatives (P1-P16). Various enaminones were obtained by the reaction of substituted acetophenones with DMF-DMA in a solvent-free environment [35,36]. Pyrazole derivatives (P1-P11) were obtained, when substituted enaminones were reacted with hydrazine hydrate 99% in presence of absolute alcohol.…”

Section: Resultsmentioning

confidence: 99%

Enaminone-Derived Pyrazoles with Antimicrobial Activity

et al. 2019

A series of pyrazoles derived from the substituted enaminones were synthesized and were evaluated for antimicrobial activity. All the compounds were characterized by the spectral data and elemental analysis. The synthesized compounds were initially screened for their antimicrobial activity against ATCC 6538, NCTC 10400, NCTC 10418, and ATCC 27853. During initial screening, compounds (P1, P6, and P11) presented significant antimicrobial activity through disc diffusion assay. These compounds were further evaluated for antimicrobial activity at different time points against Gram-positive and Gram-negative bacteria and presented significant activity for 6 hours. The activity was found to be greater against Gram-positive bacteria. In contrast at 24 hours, the activity was found only against Gram-positive bacteria except compound (P11), showing activity against both types of bacteria. Compound (P11) was found to have highest activity against both Gram-positive and Gram-negative bacteria.

“…e hybrid compounds containing these two important moieties (dihydropyrimidinone and phthalimide) may have a substantial therapeutic potential. In continuation of our work on dihydropyrimidinones, a series of novel phthalimide dihydropyrimidinone hybrids were synthesized by simple method and fully characterized by elemental analysis and spectral data [18,19].…”

Section: Introductionmentioning

confidence: 99%

Biginelli Synthesis of Novel Dihydropyrimidinone Derivatives Containing Phthalimide Moiety

et al. 2020

A new series of novel Biginelli compounds, 5-benzoyl-substituted phenyl-3,4-dihydropyrimidin-2(1H)-one-1H-isoindole-1,3(2H)-dione (1−10), were synthesized from enaminone, 2-{4-[(2E)-3-(dimethylamino)prop-2-enoyl]phenyl}-1H-isoindole-1,3(2H)-dione (IV), which was synthesized by refluxing 2-(4-acetylphenyl)-1H-isoindole-1,3(2H)-dione (III), with dimethylformamide-dimethylacetal (DMF-DMA) without solvent for 12 h. The compound 2-(4-acetylphenyl)-1H-isoindole-1,3(2H)-dione (III) was obtained by reacting phthalic anhydride (I) with para-aminoacetophenone (II) in glacial acetic acid for 2 h. The dihydropyrimidinone derivatives containing phthalimide moiety (1–10) were obtained by reacting enaminone, 2-{4-[(2E)-3-(dimethylamino) prop-2-enoyl] phenyl}-1H-isoindole-1,3(2H)-dione (IV), with urea and different substituted benzaldehydes in the presence of glacial acetic acid for 3 h. Simple and efficient method was employed to synthesize the dihydropyrimidinone derivatives containing phthalimide moiety. Structures of all the synthesized compounds were characterized by spectroscopic methods.