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

ABSTRACT: 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.

SUBMITTER: Cermola F 

PROVIDER: S-EPMC8074166 | biostudies-literature | 2021 Apr

REPOSITORIES: biostudies-literature

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

Cermola Flavio F   Vella Serena S   DellaGreca Marina M   Tuzi Angela A   Iesce Maria Rosaria MR  

Molecules (Basel, Switzerland) 20210417 8

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]  ...[more]