Suzuki–Miyaura Reactions of (4-bromophenyl)-4,6-dichloropyrimidine through Commercially Available Palladium Catalyst: Synthesis, Optimization and Their Structural Aspects Identification through Computational Studies

Malik, Ayesha; Rasool, Nasır; Kanwal, Iram; Hashmı, Muhammad Alı; Zahoor, Ameer Fawad; Ahmad, Gulraız; Altaf, Ataf Ali; Sultan, Sadia; Zakaria, Zainul Amiruddin

doi:10.3390/pr8111342

Cited by 17 publications

(16 citation statements)

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“…and 9048.28 a.u., respectively, showing the highest NLO responses, while the remaining compounds show very small hyperpolarizability values. Our research group reported N-heterocyclic derivatives having smaller values of hyperpolarizability as compared to the compounds in this study ( 4a – 4n ) [ 34 ].…”

Section: Resultsmentioning

confidence: 93%

“…From the computational point of view, these methods have become very popular in recent years because they can attain similar accuracy to the ab initio methods in less time and at a lower computational cost [ 33 ]. The optimization of the molecules ( 4a – 4n ) was accomplished with the PBE0-D3BJ/def2-TZVP/SMD 1,4-dioxane level of theory [ 34 ] which is widely used for providing accurate geometries and electronic properties for a large number of molecules. The solvent model density (SMD) is a polarizable continuum model that includes the full solute electron density without defining partial atomic charges.…”

Section: Resultsmentioning

confidence: 99%

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Facile Synthesis of 5-Aryl-N-(pyrazin-2-yl)thiophene-2-carboxamides via Suzuki Cross-Coupling Reactions, Their Electronic and Nonlinear Optical Properties through DFT Calculations

et al. 2021

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Synthesis of 5-aryl-N-(pyrazin-2-yl)thiophene-2-carboxamides (4a–4n) by a Suzuki cross-coupling reaction of 5-bromo-N-(pyrazin-2-yl)thiophene-2-carboxamide (3) with various aryl/heteroaryl boronic acids/pinacol esters was observed in this article. The intermediate compound 3 was prepared by condensation of pyrazin-2-amine (1) with 5-bromothiophene-2-carboxylic acid (2) mediated by TiCl4. The target pyrazine analogs (4a–4n) were confirmed by NMR and mass spectrometry. In DFT calculation of target molecules, several reactivity parameters like FMOs (EHOMO, ELUMO), HOMO–LUMO energy gap, electron affinity (A), ionization energy (I), electrophilicity index (ω), chemical softness (σ) and chemical hardness (η) were considered and discussed. Effect of various substituents was observed on values of the HOMO–LUMO energy gap and hyperpolarizability. The p-electronic delocalization extended over pyrazine, benzene and thiophene was examined in studying the NLO behavior. The chemical shifts of 1H NMR of all the synthesized compounds 4a–4n were calculated and compared with the experimental values.

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Section: Resultsmentioning

confidence: 93%

Section: Resultsmentioning

confidence: 99%

Facile Synthesis of 5-Aryl-N-(pyrazin-2-yl)thiophene-2-carboxamides via Suzuki Cross-Coupling Reactions, Their Electronic and Nonlinear Optical Properties through DFT Calculations

et al. 2021

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“…The new structures are combinations of pyrimidine–hydrazone, dihydronaphthalene and alkylamine chain groups. Pyrimidine is a well-known aromatic, heterocyclic organic compound with many different biological functions [ 3 , 28 , 29 ].…”

Section: Resultsmentioning

confidence: 99%

Novel Pyrimidine Derivatives as Potential Anticancer Agents: Synthesis, Biological Evaluation and Molecular Docking Study

Tylińska

Wiatrak

Czyżnikowska

et al. 2021

IJMS

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In the present paper, new pyrimidine derivatives were designed, synthesized and analyzed in terms of their anticancer properties. The tested compounds were evaluated in vitro for their antitumor activity. The cytotoxic effect on normal human dermal fibroblasts (NHDF) was also determined. According to the results, all the tested compounds exhibited inhibitory activity on the proliferation of all lines of cancer cells (colon adenocarcinoma (LoVo), resistant colon adenocarcinoma (LoVo/DX), breast cancer (MCF-7), lung cancer (A549), cervical cancer (HeLa), human leukemic lymphoblasts (CCRF-CEM) and human monocytic (THP-1)). In particular, their feature stronger influence on the activity of P-glycoprotein of cell cultures resistant to doxorubicin than doxorubicin. Tested compounds have more lipophilic character than doxorubicin, which determines their affinity for the molecular target and passive transport through biological membranes. Moreover, the inhibitory potential against topoisomerase II and DNA intercalating properties of synthesized compounds were analyzed via molecular docking.

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“…The product from the reaction mixture was purified by CC. The synthesized product was analyzed by 1 H-NMR, 13 C-NMR, and elemental analysis [30,31]. The 5-bromo-N-(5-methyl-pyrazol-3-yl)thiophene-2-carboxamide (1 eq.…”

Section: Synthesis Of N-(5-methyl-1h-pyrazol-3-yl)-5-(p-tolyl)thiophene-2-carboxamide (8b)mentioning

confidence: 99%

Synthesis of Functionalized Thiophene Based Pyrazole Amides via Various Catalytic Approaches: Structural Features through Computational Applications and Nonlinear Optical Properties

et al. 2022

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In the present study, pyrazole-thiophene-based amide derivatives were synthesized by different methodologies. Here, 5-Bromothiophene carboxylic acid (2) was reacted with substituted, unsubstituted, and protected pyrazole to synthesize the amide. It was observed that unsubstituted amide (5-bromo-N-(5-methyl-1H-pyrazol-3-yl)thiophene-2-carboxamide (7) was obtained at a good yield of about 68 percent. The unsubstituted amide (7) was arylated through Pd (0)-catalyzed Suzuki–Miyaura cross-coupling, in the presence of tripotassium phosphate (K3PO4) as a base, and with 1,4-dioxane as a solvent. Moderate to good yields (66–81%) of newly synthesized derivatives were obtained. The geometry of the synthesized compounds (9a–9h) and other physical properties, like non-linear optical (NLO) properties, nuclear magnetic resonance (NMR), and other chemical reactivity descriptors, including the chemical hardness, electronic chemical potential, ionization potential, electron affinity, and electrophilicity index have also been calculated for the synthesized compounds. In this study, DFT calculations have been used to investigate the electronic structure of the synthesized compounds and to compute their NMR data. It was also observed that the computed NMR data manifested significant agreement with the experimental NMR results. Furthermore, compound (9f) exhibits a better non-linear optical response compared to all other compounds in the series. Based on frontier molecular orbital (FMO) analysis and the reactivity descriptors, compounds (9c) and (9h) were predicted to be the most chemically reactive, while (9d) was estimated to be the most stable among the examined series of compounds.

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Suzuki–Miyaura Reactions of (4-bromophenyl)-4,6-dichloropyrimidine through Commercially Available Palladium Catalyst: Synthesis, Optimization and Their Structural Aspects Identification through Computational Studies

Cited by 17 publications

References 55 publications

Facile Synthesis of 5-Aryl-N-(pyrazin-2-yl)thiophene-2-carboxamides via Suzuki Cross-Coupling Reactions, Their Electronic and Nonlinear Optical Properties through DFT Calculations

Facile Synthesis of 5-Aryl-N-(pyrazin-2-yl)thiophene-2-carboxamides via Suzuki Cross-Coupling Reactions, Their Electronic and Nonlinear Optical Properties through DFT Calculations

Novel Pyrimidine Derivatives as Potential Anticancer Agents: Synthesis, Biological Evaluation and Molecular Docking Study

Synthesis of Functionalized Thiophene Based Pyrazole Amides via Various Catalytic Approaches: Structural Features through Computational Applications and Nonlinear Optical Properties

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