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Title: Synthesis, structural and electrochemical characterization of novel ferrocene-containing tetrahydropyrimidin-2(1H)-ones
Authors: Minić, Aleksandra
Pešić, Marko
Novakovic, Sladjana B.
Bogdanovic, Goran A.
Todosijević A.
Ilić Komatina D.
Stevanović, Dragana
Issue Date: 2020
Abstract: © 2020 Elsevier B.V. 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.
Type: article
DOI: 10.1016/j.jorganchem.2020.121422
ISSN: 0022-328X
SCOPUS: 2-s2.0-85089028968
Appears in Collections:Faculty of Science, Kragujevac

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