5-acetyl-3,4-dihydro-4-ferrocenyl-6-methylpyrimidin-2(1H)-thione | 1242447-74-0

• 英文名称: 5-acetyl-3,4-dihydro-4-ferrocenyl-6-methylpyrimidin-2(1H)-thione
• CAS: 1242447-74-0
• 化学式: C₁₇H₁₈FeN₂OS
• 分子量: 354.256
• InChiKey: OXXPKSHXWKOJGY-IDMXKUIJSA-N

反应信息

• 作为产物：
  描述：

  、 乙酰丙酮 在 silicomolybdic heteropolyacid 、 溶剂黄146 作用下， 反应 2.0h， 生成 5-acetyl-3,4-dihydro-4-ferrocenyl-6-methylpyrimidin-2(1H)-thione
  参考文献：
  名称：

  One-pot synthesis of ferrocenyl-pyrimidones using a recyclable molibdosilicic H4SiMo12O40 heteropolyacid

  摘要：

  通过甲酰基二茂铁、1,3-二羰基成分和脲/硫脲的一锅 Biginelli 反应，制备了一系列含二茂铁的二氢嘧啶（DHPs）。该反应由商用 Keggin 杂多酸（H4SiMo12O40）催化，它是一种安全、清洁且可回收的催化剂。为了提高反应的产率并阐明其机理，我们研究了三种不同的合成方案。此外，还分离出了竞争性 Knoevenagel 反应的中间产物。该方法操作简单，能以非常高的产率获得含有二茂铁的高取代二氢嘧啶。催化剂可以使用和回收，而不会明显丧失催化活性。

  DOI：

  10.1007/s11164-015-2067-5

文献信息

• New ferrocenyl-substituted heterocycles. Formation under Biginelli conditions, DFT modelling, and structure determination
  作者：K. Kiss、A. Csámpai、P. Sohár

  DOI：10.1016/j.jorganchem.2010.04.036

  日期：2010.7

  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.