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A new route to the synthesis of pyrazole and pyrimidine C-nucleoside derivatives

✍ Scribed by Carlo F Morelli; Manferdini Monica; Augusto C Veronese

Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
730 KB
Volume
55
Category
Article
ISSN
0040-4020

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✦ Synopsis

A new route to the synthesis of pyrazole and pyrimidine C-nucleosides, which involves as the key step a metal promoted reaction of ~-D-ribofuranosyl ketoesters with alkyl cyanoformates is described. 2,3,5-Tri-O-benzoyl-~-D-ribofuranosyl cyanide I reacts with ct-bromoesters, in the presence of zinc dust, to give 13-D-ribofuranosyl-enaminoesters 2 which are hydrolysed with I N hydrochloric acid to !3-ketoesters 3. The reactions of 13-ketoesters 3 with alkyl cyanoformates, in the presence of tin(IV) chloride or of catalytic amounts of metal acetylacetonates, afford l~-D-ribofuranosyl enaminoketoesters 4. These compounds react with benzylhydrazine and acetamidine to give pyrazole and pyrimidine C-nucleosides (6,7).

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