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A One-Pot Approach to Novel Pyridazine C-Nucleosides
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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.
Title: A One-Pot Approach to Novel Pyridazine C-Nucleosides
Description:
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.
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