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 MoreContact:+1-284-4950244
Address:Box 3069, Road Town, Tortola, British Virgin Islands
Shanghai PotentPharm Science and Technology Co.,Ltd
Contact:86-021-51969655
Address:Unit B, Building 18, No.300, Chuantu Rd,Pudong District, Shanghai 201202, China
ALPHA PHARMACEUTICAL CO，LTD JIANGSU
Contact:+86-527-84829968,+86-527-84829998
Address:suqian city
NanJing KaiHeng Chemical CO., LTD.
Contact:+86-25-85768391
Address:RM.1704, D, WANDA PLAZA, NO.110, MIDDLE JIANGDONG ROAD, NANJING, CHINA
Contact:0311-13263231263
Address:jian hua street,Shijiazhuang City, China
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)
