Issue 0, 1984

C-nucleoside studies. Part 17. The synthesis of 3(5)-carbamoyl-5(3)-β-D ribofuranosylpyrazole (4-deoxypyrazofurin) and 4-amino-3(5)-carbamoyl-5(3)-β-D-ribofuranosylpyrazole

Abstract

4-Amino-3(5)-cyano-5(3)-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)pyrazole (10) was converted into the diazopyrazole (11) by treatment with nitrous acid. On photolysis in aqueous dioxane using visible light compound (11) gave 3(5)-cyano–5(3)-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)pyrazole (12)[48% from (10)] which formed the corresponding amide (13)(75%) with alkaline hydrogen peroxide. Deprotection of compound (13) with methanolic ammonia afforded 3(5)-carbamoyl-5(3)-β-D-ribofuranosylpyrazole (4)(74%), the 4-deoxy analogue of pyrazofurin (3).

3(5)-Cyano-4-nitro-5(3)-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)pyrazole (1) reacted with dihydropyran and toluene-p-sulphonic acid to give the N-tetrahydropyranyl derivative (21)(66.5%). Hydrolysis of the nitrile group of compound (21), using alkaline hydrogen peroxide, afforded the amide (22)(71%) which was deprotected to give 3(5)-carbamoyl-4-nitro-5(3)-β-D-ribofuranosylpyrazole (23)(83%). Catalytic reduction of compound (23) gave 4-amino-3(5)-carbamoyl-5(3)-β-D-ribofuranosylpyrazole (5)(83%) which could be converted into formycin B (24)(69%).

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1984, 2367-2370

C-nucleoside studies. Part 17. The synthesis of 3(5)-carbamoyl-5(3)-β-D ribofuranosylpyrazole (4-deoxypyrazofurin) and 4-amino-3(5)-carbamoyl-5(3)-β-D-ribofuranosylpyrazole

J. G. Buchanan, N. K. Saxena and R. H. Wightman, J. Chem. Soc., Perkin Trans. 1, 1984, 2367 DOI: 10.1039/P19840002367

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Spotlight

Advertisements