Experimental and theoretical studies on the reactions of 1-amino-5-benzoyl-4-phenyl-1H-pyrimidine-2-one/-thione compounds with ethyl acetoacetate

Önal, Zülbiye; Yıldırım, İsmail; Kandemi̇rlı, Fatma; Arslan, Taner

doi:10.1007/s11224-010-9615-9

Cited by 11 publications

(4 citation statements)

References 27 publications

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“…All other reagents were purchased from Merck, Fluka, Aldrich and used without further purification. The starting material was prepared according to the literature procedure that described by Altural and co-workers [17][18][19][20]. A solution of 5-benzoyl-4-phenyl-pyrimidine-2(1H)-one (0.30 g, 1.1 mmol) in DMF and phosphorusoxychloride (2 ml) was heated under reflux on a steam bath for 3 h and the reaction mixture poured gradually on to crashed ice.…”

Section: Synthesismentioning

confidence: 99%

Structure of 5-benzoyl-4-phenyl-2-chloropyrimidine studied by X-ray diffraction, DFT calculations, NMR and FT-IR spectra

İnkaya

Di̇nçer

Şahan

et al. 2012

Journal of Molecular Structure

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Section: Synthesismentioning

confidence: 99%

Structure of 5-benzoyl-4-phenyl-2-chloropyrimidine studied by X-ray diffraction, DFT calculations, NMR and FT-IR spectra

İnkaya

Di̇nçer

Şahan

et al. 2012

Journal of Molecular Structure

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“…N-aminopyrimidine-2-one derivatives appear to be an important starting compound in synthetic organic chemistry. In recent years, the reactions of aminopyrimidine-2-one derivatives with anhydrides (27), isothiocyanate, isocyanate (28), carbonyl compounds (29), acyl chlorides (30), benzaldehydes derivatives (Schiff bases) and transition metal complexes (31)(32)(33)(34) have been reported in different solvents and at various temperatures. Nowadays, theoretical and experimental comparison of N-aminopyrimidine-2-one derivatives has become popular (35)(36)(37).…”

Section: Introductionmentioning

confidence: 99%

Could pyrimidine derivative be effective against Omicron of SARS-CoV-2?

Karatas¹,

Tüzün²,

Kökbudak³

2022

BLL

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BACKGROUND: A pyrimidine based Schiff base was examined in this report. Structural and spectral characterizations were done with Gaussian software. Active sites of the compound were determined using molecular electrostatic potential (MEP) maps. AIM: We focused to determine whether pyrimidine based Schiff base would be an inhibitor against Omicron of SARS-CoV-2 in silico. RESULTS AND CONCLUSION: As one of the perils the world has seen lately, omicron of SARS-CoV-2, is a complication to be solved. For the sake of that, anti-viral properties of studied pyrimidine based Schiff base compound were investigated with molecular docking calculations. It was found that the quantitative values of the calculated parameters were in the applicable ranges. In accordance with these results, it will be an important guide for future in vitro and in vivo analysis (Tab. 3, Fig. 7, Ref. 70).

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“…Schiff bases are well‐known compounds and are commonly used in industrial and biological area as a reaction intermediate. The possible reaction mechanism of the Schiff base formation and the effect of the solvent effect, pH, and type of reactants have also been explained theoretically .…”

Section: Introductionmentioning

confidence: 99%

Density Functional Study of the Reaction Mechanism of Two Oxiimine Alcohol Formations and Their Novel Rearrangements

Kaya

2016

Helvetica Chimica Acta

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In this study, the reaction mechanisms of isonitrosoacetophenone (inapH) with ethanolamine (ea) and 1‐phenylethanolamine (pea) have been investigated theoretically using B3LYP/6‐311G(d,p) method to explain why the formation and unexpected rearrangement products occur or not occur. While the reaction between isonitrosoacetophenone (inapH) with ethanolamine gives oximine alcohol (Ib), the reaction of 1‐phenylethanolamine with inapH results in the formation of oximine alcohol with a different substituent (Ia) and amido alcohol (IIa), which is the unexpected rearrangement product. The rearrangement driving forces of compounds from Ia to IIa are calculated as ca. 28 and 23 kJ/mol in the gas and EtOH phases, respectively. These driving forces have been calculated ca. 46 and 45 kJ/mol for the rearrangement of compound Ib to obtain IIb in the same phases, respectively. This high driving force shows that the compound IIb cannot be obtained from rearrangement of compound Ib as described experimentally in the literature. In addition, as the DFT functionals poorly describe dispersion effects, dispersion correction for reaction heat and free‐energy barrier was estimated using the wB97X‐D/6‐311G(d,p). In general, the relative free energies of all molecules calculated from wB97XD method are lower than performed from B3LYP level. The changes of thermodynamic properties for all molecules with temperature ranging from 100 to 500 K have been obtained using the statistical thermodynamic method.

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Experimental and theoretical studies on the reactions of 1-amino-5-benzoyl-4-phenyl-1H-pyrimidine-2-one/-thione compounds with ethyl acetoacetate

Cited by 11 publications

References 27 publications

Structure of 5-benzoyl-4-phenyl-2-chloropyrimidine studied by X-ray diffraction, DFT calculations, NMR and FT-IR spectra

Structure of 5-benzoyl-4-phenyl-2-chloropyrimidine studied by X-ray diffraction, DFT calculations, NMR and FT-IR spectra

Could pyrimidine derivative be effective against Omicron of SARS-CoV-2?

Density Functional Study of the Reaction Mechanism of Two Oxiimine Alcohol Formations and Their Novel Rearrangements

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