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

✍ Scribed by Augusto C Veronese; Carlo F Morelli

Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
191 KB
Volume
39
Category
Article
ISSN
0040-4039

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✦ Synopsis

A new route to the synthesis of pyrazole and pyrimidine C-nucleosides, involving as the key step a metal catalysed reaction of [3-D-ribofuranosyl ketoesters with alkyl cyanoformates, is described. 2,3,5-Tri-O-benzoyl-13-D-ribofuranosyl cyanide (1) reacts with Β’t-bromoesters, in the presence of zinc dust, to give [3-D-ribofuranosyl-enaminoesters 2 which are easily hydrolised to ~-ketoesters 3. The reactions of compounds 3 with alkyl cyanoformates, in the presence of catalytic amounts of [Cu(acac)2], afford C-glycosyl enaminoketosters 4. These compounds react with benzylhydrazine and acetamidine to give pyrazole and pyrimidine C-nucleosides 5 and 6 respectively.

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