Synthesis, structural and electrochemical characterization of novel ferrocene-containing tetrahydropyrimidin-2(1H)-ones

• Published in: Journal of organometallic chemistry 2020-09, Vol.923, p.121422, Article 121422
• Main Authors: Minić, Aleksandra, Pešić, Marko S., Novaković, Sladjana B., Bogdanović, Goran A., Todosijević, Anka, Komatina, Danijela Ilić, Stevanović, Dragana
• Format: Article
• Language: English
• Subjects: Crystal structure; Electrochemistry; Ferrocene; One-pot reaction; Tetrahydropyrimidin-2(1H)-ones
• ISSN: 0022-328X; 1872-8561
• DOI: 10.1016/j.jorganchem.2020.121422

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. [Display omitted] •A one-pot procedure for the preparation of 1-aryl-4-ferrocenyltetrahidropyrimidin-2(1H)-ones has been developed.•Eleven novel ferrocene-containing tetrahydropyrimidin-2(1H)-ones were synthesized in good to high yields (up to 93%).•All products have been isolated in high purity >95% and a detailed spectroscopic characterization has been provided.•A detailed single-crystal X-ray diffraction analysis was successfully performed on three examples.•Electrochemical behavior of newly synthesized has been evaluated by the usage of cyclic voltammetry.