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Synthesis, structural and electrochemical characterization of novel ferrocene-containing tetrahydropyrimidin-2(1H)-ones
Journal of Organometallic Chemistry ( IF 2.1 ) Pub Date : 2020-07-08 , DOI: 10.1016/j.jorganchem.2020.121422
Aleksandra Minić , Marko S. Pešić , Sladjana B. Novaković , Goran A. Bogdanović , Anka Todosijević , Danijela Ilić Komatina , Dragana Stevanović

Herein, we report an easy performable method for the synthesis of ferrocene-containing tetrahydropyrimidin-2(1H)-ones starting from the corresponding 3-arylamino-1-ferrocenylpropan-1-ols and sodium cyanate (NaOCN) in the presence of glacial acetic acid. The protocol is included an intramolecular cyclization of an in situ generated 1,3-hydroxyurea. The scope of the reaction towards eleven ferrocene-containing 1,3-amino alcohols has been explored and the targeted 1-aryl-4-ferrocenyltetrahidropyrimidin-2(1H)-ones were obtained in good to high yields (up to 93%). All products have been isolated in high purity >95%. In addition, we have provided a detailed structural characterization of the new compounds, which has been performed by IR and NMR spectroscopy. The single-crystal X-ray diffraction analysis was successfully performed on three representative examples, as well as elemental analysis. Moreover, molecular structure properties and intermolecular interactions of these three structures have been compared and analyzed in detail. Electrochemical properties of products were investigated by cyclic voltammetry. This investigation revealed the quasi-reversible one-electron redox process.



中文翻译:

新型含二茂铁的四氢嘧啶-2(1 H)-ones的合成,结构和电化学表征

在此,我们报告了在冰川存在下,从相应的3-芳基氨基-1-二茂铁基丙烷-1-醇和氰酸钠(NaOCN)出发,易于合成含二茂铁的四氢嘧啶-2(1 H)-的简便方法。醋酸。该方案包括原位产生的1,3-羟基脲的分子内环化。已探究了针对11种含二茂铁的1,3-氨基醇的反应范围,并针对了1-芳基-4-二茂铁基四氢嘧啶2(1 H)-以高到高的产率(高达93%)获得。所有产品均以> 95%的高纯度分离。此外,我们提供了新化合物的详细结构特征,已通过IR和NMR光谱进行了表征。在三个代表性实例上成功进行了单晶X射线衍射分析以及元素分析。此外,已经对这三种结构的分子结构性质和分子间相互作用进行了比较和详细分析。用循环伏安法研究产物的电化学性能。这项研究揭示了准可逆的单电子氧化还原过程。

更新日期:2020-07-08
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