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DOI: 10.1039/A707079I (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 1, 1998, 947-954

Syntheses of C- and N-nucleosides from 1-aza-2-azoniaallene and 1,3-diaza-2-azoniaallene salts

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Najim Al-Masoudi, Nasser A. Hassan, Yaseen A. Al-Soud, Patrick Schmidt, Alaa El-Din M. Gaafar, Min Weng, Stefano Marino, Annette Schoch, Atef Amer and Johannes C. Jochims

Abstract

C-Nucleosides are prepared by cycloaddition of 1-aza-2-azoniaallene salts 2 and 1,3-diaza-2-azoniaallene salts 5 to the triple bonds of a glycosylalkyne and of glycosyl cyanides. Thus, the glucosylalkyne 7 reacts with salts 5 to give the 4-glucosyl-1,2,3-triazolium salt 8. From the galactosyl cyanide 9, the ribofuranosyl cyanide 13, and several 1-aza-2-azoniaallene salts 2 the glycosyl-1,2,4-triazoles 11, 15, 17 are obtained. Deacylation affords the free C-nucleosides 12, 16, 18. Cycloaddition to the C[double bond, length half m-dash]S double bond of the glucosyl isothiocyanate 19 furnishes glucosylimino-1,3,4-thiaziazoles 20–22. A new method for the preparation of the isothiocyanate 19 is described.

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