C-Nucleoside studies. Part XI. Cine-substitution in 1,4-dinitropyrazoles; application to the synthesis of formycin via nitropyrazole derivatives
- 1 December 1980
- journal article
- research article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 58 (23) , 2624-2627
- https://doi.org/10.1139/v80-419
Abstract
Reaction of 1,4-dinitro-3-methylpyrazole with a variety of nucleophiles led to the formation of 5-substituted 3-methyl-4-nitropyrazoles 11–15 by a process of cine-substitution. This reaction has been applied as the key step in a novel synthesis of formycin. Treatment of 1,4-dinitro-3-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)pyrazole (17) with cyanide ion produced 3(5)-cyano-4-nitro-5(3)-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)pyrazole (19) in 89% yield. Catalytic reduction to the 4-amino compound 20 (84%), and subsequent reaction with formamidine acetate yielded formycin triacetate 21 (79%). Methanolysis of 21 produced formycin (1) in 90% yield.This publication has 3 references indexed in Scilit:
- C-nucleoside studies. Part 8. Synthesis of 3-β-D-arabinofuranosylpyrazole fromD-mannoseJournal of the Chemical Society, Perkin Transactions 1, 1979
- C-nucleoside studies. Part 7. A new synthesis of showdomycin, 2-β-D-ribofuranosylmaleimideJournal of the Chemical Society, Perkin Transactions 1, 1979
- C-nucleoside studies. Part 6. Synthesis of 3-[2,3,5-tri-O-benzyl-β-(and α)-D-ribofuranosyl]prop-2-yn-1-ol and related compounds; a new synthesis of 3(5)-(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)pyrazoleJournal of the Chemical Society, Perkin Transactions 1, 1977