Journal of the Chemical Society. Perkin transactions I p. 2374 - 2378 (1981)
Update date:2022-08-04
Topics:
Buchanan, J. Grant
Stobie, Alan
Wightman, Richard H.
Treatment of 3-cyano-4-nitro-5-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)pyrazole (4) with benzyl bromide and triethylamine gave as major product the 1-benzyl-5-cyano-isomer (5), whilst similar treatment of 5-cyano-3-methyl-4-nitropyrazole (7) gave exclusively 1-benzyl-3-cyano-5-methyl-4-nitropyrazole (8).This was converted into 4-amino-1-benzyl-3-carboxamido-5-methylpyrazole (10); attempts to convert (10) into a 4-hydroxypyrazole via the diazonium salt were unsuccessful, but photolysis of the diazonium salt (11) in aqueous trifluoroacetic acid-dioxan gave 1-benzyl-3-carboxamido-5-methylpyrazole (13) in 67percent yield.Treatment of 4-amino-3-cyano-5-methylpyrazole (14) with nitrous acid and subsequent neutralisation gave a diazopyrazole which on photolysis in aqueous acetone yielded 3-cyano-4-hydroxy-5-methylpyrazole (16) in 79percent overall yield.Application of the same sequence to 4-amino-3-cyano-5-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-pyrazole (2) gave the 4-hydroxy-compound (17) (87percent overall), which was converted in two steps into pyrazofurin (1).
View MoreBeijing Century Richap Chemistry Co.,Ltd
Contact:+86- 010-64455497
Address:Guannan County, Lianyungang City, Jiangsu Province, China
Huangshi Meifeng Chemical Co.,ltd.
Contact:+86-714-6516706
Address:1941-4-3#,Hubin Avenue,Huangshi,Hubei,China
Liao Cheng All Win Chemicals Co.,LTD
Contact:86+0635-2991582
Address:Room 402,Unit 1,No.27 building.Zhong tong shi dai haoyuan,liaocheng city,Shan dong Province.China
Xiamen Huasing Chemicals Co.Ltd.
Contact:0086-592-6228397
Address:NO.24, Xinglin North 2nd Road,Jimei district
Contact:+86-570-4336358
Address:No.87 Building,Tianqian,Sidu Town
Doi:10.1021/jm00144a015
(1981)Doi:10.1016/S0008-6215(00)85303-3
(1981)Doi:10.1021/ja01316a035
(1934)Doi:10.1021/ol0485060
(2004)Doi:10.1016/S0022-328X(00)80129-1
(1981)Doi:10.1021/ja01169a508
(1949)
