N,N-diethyl-1,2,3,4-tetrahydro-6-methyl-4-ferrocenyl-2-thioxopyrimidine-5-carboxamide | 1242447-82-0

• 英文名称: N,N-diethyl-1,2,3,4-tetrahydro-6-methyl-4-ferrocenyl-2-thioxopyrimidine-5-carboxamide
• CAS: 1242447-82-0
• 化学式: C₂₀H₂₅FeN₃OS
• 分子量: 411.351
• InChiKey: VEBSOGGDXIIGEV-GXKRWWSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
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• 重原子数：
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• 可旋转键数：
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• 环数：
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• sp3杂化的碳原子比例：
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• 拓扑面积：
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• 氢给体数：
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• 氢受体数：
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反应信息

• 作为产物：
  描述：

  二茂铁甲醛 、 硫脲 、 N,N-二乙基乙酰乙酰胺 在 硼酸 作用下， 以 溶剂黄146 为溶剂， 以50%的产率得到N,N-diethyl-1,2,3,4-tetrahydro-6-methyl-4-ferrocenyl-2-thioxopyrimidine-5-carboxamide
  参考文献：
  名称：

  New ferrocenyl-substituted heterocycles. Formation under Biginelli conditions, DFT modelling, and structure determination

  摘要：

  A series of novel ferrocene-containing-dihydropyrimidines (DHPs) were prepared by three-component Biginelli reactions of formylferrocene, 1,3-dioxo-components and thiourea catalyzed by boric acid and ytterbium triflate, respectively. When cyclic-1,3-diones were employed as dioxo component in the reactions promoted by boric acid, besides one expected 4-ferrocenyl-2-thioxoquinazoline, 9-ferrocenyl-2H-xanthene-1,8-dione and 9-ferrocenylcyclopenta[b]chromen-8-ones could also be isolated as products. By means of control reactions and B3LYP/6-31 G(d) modelling the formation of the chromenone was interpreted by hetero-DielseAlder addition involving the Knoevenagel intermediate and the cyclopentadiene resulted in situ from acid-catalyzed decomposition of formylferrocene. The enhanced tendency of the acyclic dioxo components to undergo Biginelli reaction avoiding cycloaddition was reasoned by the formation of Knoevenagel intermediates capable of chelating proton or Lewis acids. The structures of the new compounds were established by IR and NMR spectroscopy, including HMQC, HMBC, DEPT and DNOE measurements. Some structural characteristics were disclosed by B3LYP/6-31 G (d) method. (C) 2010 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2010.04.036