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

被引：20

作者：

Morelli, CF ^{[1
]}

Manferdini, M ^{[1
]}

Veronese, AC ^{[1
]}

机构：

[1] Univ Ferrara, Dipartimento Sci Farmaceut, I-44100 Ferrara, Italy

来源：

TETRAHEDRON | 1999年 / 55卷 / 35期

关键词：

D O I：

10.1016/S0040-4020(99)00595-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new route to the synthesis of pyrazole and pyrimidine C-nucleosides, which involves as the key step a metal promoted reaction of beta-D-ribofuranosyl ketoesters with alkyl cyanoformates is described. 2,3,5-Tri-O-benzoyl-beta-D-ribofuranosyl cyanide 1 reacts with alpha-bromoesters, in the presence of zinc dust, to give beta-D-ribofuranosyl-enaminoesters 2 which are hydrolysed with IN hydrochloric acid to beta-ketoesters 3. The reactions of beta-ketoesters 3 with alkyl cyanoformates, in the presence of tin(IV) chloride or of catalytic amounts of metal acetylacetonates, afford beta-D-ribofuranosyl enaminoketoesters 4. These compounds react with benzylhydrazine and acetamidine to give pyrazole and pyrimidine C-nucleosides (6,7). (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：10803 / 10814

页数：12

共 13 条

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