Esterification vs. 1,3-Dipolar Cycloaddition Synthetic Approaches for Preparation of the Fluorescently Labelled Iron(II) Clathrochelates

Roman A. Selin,^a@1 Viktor Ya. Chernii,^a Dmytro V. Kryvorotenko,^b Andriy Mokhir,^c and Yan Z. Voloshin^d,e@2

^aV.I. Vernadskii Institute of General and Inorganic Chemistry NASU, 03080 Kyiv, Ukraine

^bInstitute of Molecular Biology and Genetics, NASU, 03680 Kyiv, Ukraine

^cOrganic Chemistry II, Friedrich-Alexander-University of Erlangen–Nuremberg, 91054 Erlangen, Germany

^dN.S. Kurnakov Institute of General and Inorganic Chemistry of the Russian Academy of Sciences, 119991 Moscow, Russia

^eA.N. Nesmeyanov Institute of the Organoelement Compounds of the Russian Academy of Sciences, 119991 Moscow, Russia

^@1Corresponding author E-mail: selin.roman.oleksandrovich@gmail.com

^@2Corresponding author E-mail: voloshin@ineos.ac.ru

DOI: 10.6060/mhc201230v

Macroheterocycles 2021 14(1) 94-100

Two most common synthetic approaches (i.e. the esterification and 1,3-dipolar cycloaddition reactions) to a functionalization of the reactive three-dimensional molecular platforms, allowing to obtain the fluorescently labelled iron(II) clathrochelates and, therefore, to study their localization and accumulation in cancer cells, were compared. Because an esterification approach gave the target complexes in a very low yield, if any, such a functionalization of a known propargylamine iron(II) clathrochelate complex with terminal C≡C bond as a reactive macrobicyclic precursor by the copper-promoted 1,3-dipolar cycloaddition “click” reaction was also tested. This one-pot synthetic procedure allowed to obtain the cumarin-terminated iron(II) cage complex in a high yield; it was characterized using elemental analysis, ESI-TOF mass, and ¹H and ¹³C{¹H} NMR spectra.

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Esterification vs. 1,3-Dipolar Cycloaddition Synthetic Approaches for Preparation of the Fluorescently Labelled Iron(II) Clathrochelates

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