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N-Fluoroalkylated Morpholinos - a New Class of Nucleoside Analogues

Debreczeni N, Hotzi J, Bege M, Lovas M, Mező E, Bereczki I, Herczegh P, Kiss L, Borbás A
Chemistry. 2022 Nov 27. doi: 10.1002/chem.202203248. Online ahead of print. PMID: 36437234
The first concise and efficient synthesis of some fluorine-containing morpholino nucleosides analogs has been developed. 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 analogs with a N-CF3 element in their structure.
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