A One-Pot Approach to Novel Pyridazine C-Nucleosides.

Flavio Cermola, Serena Vella, Marina DellaGreca, Angela Tuzi, Maria Rosaria Iesce

Molecules (Basel, Switzerland) 2021 Apr 17

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The synthesis of glycosides and modified nucleosides represents a wide research field in organic chemistry. The classical methodology is based on coupling reactions between a glycosyl donor and an acceptor. An alternative strategy for new C-nucleosides is used in this approach, which consists of modifying a pre-existent furyl aglycone. This approach is applied to obtain novel pyridazine C-nucleosides starting with 2- and 3-(ribofuranosyl)furans. It is based on singlet oxygen [4+2] cycloaddition followed by reduction and hydrazine cyclization under neutral conditions. The mild three-step one-pot procedure leads stereoselectively to novel pyridazine C-nucleosides of pharmacological interest. The use of acetyls as protecting groups provides an elegant direct route to a deprotected new pyridazine C-nucleoside.

Citation

Flavio Cermola, Serena Vella, Marina DellaGreca, Angela Tuzi, Maria Rosaria Iesce. A One-Pot Approach to Novel Pyridazine C-Nucleosides. Molecules (Basel, Switzerland). 2021 Apr 17;26(8)