A One-Pot Approach to Novel Pyridazine <em>C</em>-Nucleosides

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

Format: Article
Diterbitkan: MDPI AG 2021-04-01

Deskripsi

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 <i>C</i>-nucleosides is used in this approach, which consists of modifying a pre-existent furyl aglycone. This approach is applied to obtain novel pyridazine <i>C</i>-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 <i>C</i>-nucleosides of pharmacological interest. The use of acetyls as protecting groups provides an elegant direct route to a deprotected new pyridazine <i>C</i>-nucleoside.