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首页> 外文期刊>RSC Advances >A facile and concise route to (hydroxybenzoyl)pyrido[2,3-d]pyrimidine heterocycle derivatives: synthesis, and structural, spectral and computational exploration
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A facile and concise route to (hydroxybenzoyl)pyrido[2,3-d]pyrimidine heterocycle derivatives: synthesis, and structural, spectral and computational exploration

机译：（羟基苯甲酰基）吡啶并[2,3-d]嘧啶杂环衍生物的简便方法：合成以及结构，光谱和计算探索

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In this work, we report the efficient synthesis of novel (hydroxybenzoyl)pyrido[2,3- d ]pyrimidine heterocycle derivatives: 6-(2-hydroxy-5-methylbenzoyl)-1-methylpyrido[2,3- d ]pyrimidine-2,4(1 H ,3 H )-dione ( 6a ), 6-(5-fluoro-2-hydroxybenzoyl)-1-methylpyrido[2,3- d ]pyrimidine-2,4(1 H ,3 H )-dione ( 6b ), 6-(5-ethyl-2-hydroxybenzoyl)-1-methylpyrido[2,3- d ]pyrimidine-2,4(1 H ,3 H )-dione ( 6c ) and 6-(2-hydroxy-5-isopropylbenzoyl)-1-methylpyrido[2,3- d ]pyrimidine-2,4(1 H ,3 H )-dione ( 6d ). The chemical structures of the title compounds were ascertained by spectral techniques including ~(1) H, ~(13) C NMR, UV-visible and FT-IR spectroscopy as well as single-crystal X-ray diffraction analysis. Additionally, density functional theory (DFT) and time-dependent (TD-DFT) computation were adopted to analyze the electronic structures of 6a–d . Compounds 6a–d were computed in the ground state for FT-IR spectroscopic and natural bond orbital (NBO) analysis by DFT/B3LYP with the 6-311+G(d,p) basis set. UV-vis spectroscopic and HOMO and LUMO energy values for 6a–d were determined via TD-DFT/B3LYP with the 6-311+G(d,p) basis set. The optimized geometric parameters, UV-vis findings, and vibrational frequencies indicate good consistency with the experimental data. NBO analysis was conducted to explore the interactions and charge transfer among different orbitals in the title compounds. The HOMO and LUMO band gap (Δ E ) values for 6a–d were found to be 3.93, 3.91, 4.10 and 3.91 eV, respectively. Molecular electrostatic potential (MEP) analysis explored the reactivity of the title compounds by predicting their nucleophilic as well as electrophilic sites.
机译：在这项工作中，我们报告了新型（羟基苯甲酰基）吡啶并[2,3-d]嘧啶杂环衍生物的有效合成：6-（2-羟基-5-甲基苯甲酰基）-1-甲基吡啶并[2,3-d]嘧啶- 2,4（1 H，3 H）-二酮（6a），6-（5-氟-2-羟基苯甲酰基）-1-甲基吡啶[2,3- d]嘧啶-2,4（1 H，3 H） -二酮（6b），6-（5-乙基-2-羟基苯甲酰基）-1-甲基吡啶[2,3- d]嘧啶-2,4（1 H，3 H）-二酮（6c）和6-（2 -羟基-5-异丙基苯甲酰基）-1-甲基吡啶并[2,3-d]嘧啶-2,4（1 H，3 H）-二酮（6d）。标题化合物的化学结构通过光谱技术确定，包括〜（1）H，〜（13）NMR，紫外可见光谱和FT-IR光谱以及单晶X射线衍射分析。此外，采用密度泛函理论（DFT）和时变（TD-DFT）计算来分析6a–d的电子结构。通过DFT / B3LYP在6-311 + G（d，p）的基础下，以基态计算化合物6a-d，以进行FT-IR光谱和自然键轨道（NBO）分析。通过TD-DFT / B3LYP和6-311 + G（d，p）基集确定6a–d的紫外可见光谱以及HOMO和LUMO能量值。优化的几何参数，紫外线可见光和振动频率表明与实验数据具有良好的一致性。进行了NBO分析，以探索标题化合物中不同轨道之间的相互作用和电荷转移。发现6a–d的HOMO和LUMO带隙（ΔE）值分别为3.93、3.91、4.10和3.91 eV。分子静电势（MEP）分析通过预测标题化合物的亲核位点和亲电位点来探索其反应活性。

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