Tetrahedron p. 10803 - 10814 (1999)
Update date:2022-07-30
Topics:
Morelli, Carlo F.
Manferdini, Monica
Veronese, Augusto C.
A new route to the synthesis of pyrazole and pyrimidine C-nucleosides, which involves as the key step a metal promoted reaction of β-D- ribofuranosyl ketoesters with alkyl cyanoformates is described. 2,3,5-Tri-O- benzoyl-β-D-ribofuranosyl cyanide 1 reacts with α-bromoesters, in the presence of zinc dust, to give β-D-ribofuranosyl-enaminoesters 2 which are hydrolysed with 1N hydrochloric acid to β-ketoesters 3. The reactions of β- ketoesters 3 with alkyl cyanoformates, in the presence of tin(IV) chloride or of catalytic amounts of metal acetylacetonates, afford β-D-ribofuranosyl enaminoketoesters 4. These compounds react with benzylhydrazine and acetamidine to give pyrazole and pyrimidine C-nucleosides (6.7).
View MoreContact:+86-15850770348
Address:51 OF XIANGFANGCUN ROAD, Nanjing 210002, China
Dalian Join King Biochemical Tech. Co., Ltd.
Contact:0411 39216206
Address:814 First State Blvd
Huludao Tianqi Shengye Chemical Co.,Ltd.
Contact:0086 429 2075777
Address:Area B,Shipbuilding Industry Park,Beigang District,Huludao City,Liaoning prov.,China
Jiangxi Province Bethel Pharmaceutical Co., Ltd.
Contact:+86-795-259 3456 ,+86-15957688008 13566650571
Address:Huangjindui Chemical Park, Shanggao County ,Yichun city,Jiangxi Province
Tianjin Anda North Industrial & Business Co.Ltd.
Contact:86-22-24999306
Address:No.11 Erwei Road,Dongli Development Area,Tianjin,China
Doi:10.1016/S0014-827X(98)00006-8
(1998)Doi:10.1021/jo01088a028
(1959)Doi:10.1021/ja980702c
(1998)Doi:10.1021/jo00326a053
(1981)Doi:10.1080/00958972.2010.548862
(2011)Doi:10.1039/c0cc04677a
(2011)