Synthesis of ‘Reversed’ Pyrimidine and Pyrazolo[1,5-a]pyrimidine-C-Nucleoside Analogues from Push-Pull Functionalized α-d-xylo-Hept-5-ulofuranurononitrile

Imran Ali Hashmi; Firdous Imran Ali; Holger Feist; Manfred Michalik; Helmut Reinke; Klaus Peseke

doi:10.1055/s-2007-983879

PAPER

Synthesis of ‘Reversed’ Pyrimidine and Pyrazolo[1,5-a]pyrimidine-C-Nucleoside Analogues from Push-Pull Functionalized α-d-xylo-Hept-5-ulofuranurononitrile

Imran Ali Hashmi*^a,b, Firdous Imran Ali^a, Holger Feist^b, Manfred Michalik^c, Helmut Reinke^b, Klaus Peseke^b
^a Department of Chemistry, University of Karachi, University road, Karachi-75270, Pakistan
^b Universität Rostock, Institut für Chemie, Albert-Einstein-Str. 3a, 18059 Rostock, Germany
^c Leibniz-Institut für Organische Katalyse, Albert-Einstein-Str. 29a, 18059 Rostock, Germany
e-Mail: imran_ali_hashmi@yahoo.com;

Abstract

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Abstract

3-O-Benzyl-6-deoxy-1,2-O-isopropylidene-6-[bis(methylsulfanyl)methylene]-α-d-xylo-hept-5-ulofuranurononitrile (1) was reacted with acetamidinium chloride, S-methylisothiouronium sulfate, and guanidinium chloride, respectively, in the presence of triethylamine to furnish the 2-substituted 4-(3-O-benzyl-1,2-O-isopropylidene-α-d-xylo-tetrofuranos-4-yl)-6-methylsulfanylpyrimidine-5-carbonitriles 2a-c. Treatment of 1 with different 5-aminopyrazole-4-carboxylic acid derivatives yielded the 8-(3-O-benzyl-1,2-O-isopropylidene-α-d-xylo-tetrofuranos-4-yl)-6-methylsulfanylpyrazolo[1,5-a]pyrimidine-3,7-dicarboxylic acid derivatives 3a-c.

Key words

enzyme inhibitors - C-nucleosides - monosaccharide derivatives - cyclization - pyrazoles

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References

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