Reaction of sugars with 2-hydrazinopyridine, precursors for seco C-nucleosides of 1,2,4-triazolo[4,3-a]pyridine.
Reaction of 2-hydrazinopyridine (1) with D-xylose, D-galactose, D-glucose and D-fructose afforded the corresponding hydrazones mainly in the acyclic forms 2, 3, 6 and 11 with minor amounts of the cyclic structures. Oxidative cyclization of the hydrazones with bromine in methanol resulted in the formation of the 3-(polyhydroxyalkyl)-1,2,4-triazolo[4,3-a]pyridine derivatives 13-15 whose acetylation afforded the acetylated derivatives 16-18. Assignment of 1D and 2D NMR spectral data in addition to 15N NMR experiments led to complete characterization of the products.
El Ashry
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Chemistry Department, Faculty of Science, Alexandria University, Alexandria, Egypt. eelashry60@hotmail.com
Abdul-Ghani
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D003500:Cyclization; D006835:Hydrazones / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D015394:Molecular Structure; D009005:Monosaccharides / Q000737:chemistry*; D010084:Oxidation-Reduction; D011728:Pyridones / Q000737:chemistry*
D006835:Hydrazones; D009005:Monosaccharides; D011728:Pyridones; C062607:2-hydrazinopyridine