C-Nucleosides. 1. Synthesis of 3-(.beta.-D-ribofuranosyl)pyridazines

Maeba, Isamu; Iwata, Katsumi; Usami, F.; Furukawa, Hiroshi

doi:10.1021/jo00166a012

Cited by 52 publications

(14 citation statements)

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“…Pyridazine 5d was quite stable; however, it slowly aromatized after several days at room temperature, leading to the corresponding furan 6d ( Scheme 8 ). Similar elimination was previously observed in a benzoylated pyridazine C-nucleoside [ 18 ].…”

Section: Resultssupporting

confidence: 85%

“…The β-configuration of pyridazine 5a was confirmed by the 2D-NOESY experiment, which evidenced correlation between the H-1′ and the H-4′ of the sugar ring ( Figure 1 ). With the exception of the protecting groups, the 3-(ribofuranosyl)pyridazine 5a was the same as that reported by Maeba et al [ 18 ].…”

Section: Resultssupporting

confidence: 77%

“…In many cases, the photochemical approach represents an alternative to other methods. As an example, Maeba described the synthesis of 3-(2′,3′,5′-tri- O -benzoyl-β-ribofuranosyl)pyridazine through a series of reactions involving the oxidation of the furan ring by bromine and methanol [ 18 ]. We obtained an analogue 4-(2′,3′,5′-tri- O -acetyl-β-ribofuranosyl)-3,6-dimetylpyridazine in 70% yield (based on starting furan) by oxygenation, followed by diethyl sulfide reduction and hydrazine hydrochloride cyclization [ 16 ].…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

A One-Pot Approach to Novel Pyridazine C-Nucleosides

Cermola¹,

Vella²,

DellaGreca³

et al. 2021

Molecules

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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.

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Section: Resultssupporting

confidence: 85%

Section: Resultssupporting

confidence: 77%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

A One-Pot Approach to Novel Pyridazine C-Nucleosides

Cermola¹,

Vella²,

DellaGreca³

et al. 2021

Molecules

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show abstract

“…The synthesis of 5-nitro-2-(P-o-ribofuranosyl)furan (4) from the glycosylfuran (I ) is described. Treatment of compound (1 ) with acetyl nitrate in acetonitrile afforded compound (2) in quantitative yield. When compound (2) was treated with pyridine, acetic acid was lost from the molecule to afford the protected nitrofuran (3) in 95% yield.…”

Section: C-nucleosides Part 13t Synthesis Of 5-nitro-2-(p-~-ribofuran...mentioning

confidence: 99%

“…Treatment of compound (1 ) with acetyl nitrate in acetonitrile afforded compound (2) in quantitative yield. When compound (2) was treated with pyridine, acetic acid was lost from the molecule to afford the protected nitrofuran (3) in 95% yield. Deprotection of compound (3) with methanolic sodium hydroxide afforded three products, nitrofuran (4) and the unexpected spiro compounds (5a, b) in 29, 4, and 9% yield, respectively.…”

Section: C-nucleosides Part 13t Synthesis Of 5-nitro-2-(p-~-ribofuran...mentioning

confidence: 99%