N‐Fluoroalkylated Morpholinos – a New Class of Nucleoside Analogues

Debreczeni, Nóra and Hotzi, Judit and Bege, Miklós and Lovas, Miklós and Mező, Erika and Bakai-Bereczki, Ilona and Herczegh, Pál and Kiss, Loránd and Borbás, Anikó (2023) N‐Fluoroalkylated Morpholinos – a New Class of Nucleoside Analogues. CHEMISTRY-A EUROPEAN JOURNAL, 29 (11). No-e202203248. ISSN 0947-6539

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Abstract

The first concise and efficient synthesis of some fluorine-containing morpholino nucleosides has been devel- oped. One synthetic strategy was based on the oxidative ring cleavage of the vicinal diol unit of uridine, cytidine adenosine and guanosine derivatives, followed by cyclisation of the dialdehyde intermediates by double reductive amination with fluorinated primary amines to obtain various N-fluoroalkylated morpholinos. Another approach involved cyclisation of the diformyl intermediates with ammonia source, followed by dithiocarbamate formation and desulfurization-fluorination with diethylaminosulfur trifluoride yielding the corresponding morpholine-based nucleoside analogues with a N-CF3 element in their structure.

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