C-nucleoside studies. Part 20. Synthesis of some pyrazolo[4,3-d]pyrimidine acyclonucleosides related to (S)-(2,3-dihydroxypropyl)adenine; a direct method for double functionalization of the pyrazole ring
- 1 January 1989
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 5,p. 925-930
- https://doi.org/10.1039/p19890000925
Abstract
Treatment of 3(5)-alkylpyrazoles with ammonium nitrate and trifluoroacetic anhydride in trifluoroacetic acid gives 3-alkyl-1,4-dinitropyrazoles directly. This procedure, in conjunction with cine-substitution, offers a direct route for double functionalisation of the pyrazole ring. 3(5)-Cyano-5(3)-[(S)-2,3-diacetoxypropyl]-4-nitropyrazole (13), prepared in this way, was elaborated into 5-amino-3-[(S)-2,3-dihydroxypropyl]-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one (5), 7-amino-3-[(S)-2,3-dihydroxypropyl]-1H-6-methylpyrazolo[4,3-d]pyrimidin-5(6H)-one (6), its Ndemethyl analogue (7), and 4-amino-5-carbamoyl-3-[(S)-2,3-dihydroxypropyl]pyrazole (8), all of which are C-nucleoside analogues of the antiviral agent (S)-9-(2,3-dihydroxypropyl)adenine (4).Keywords
This publication has 9 references indexed in Scilit:
- Heterocyclic synthesis via a 1,3-dicyclohexylcarbodiimide-mediated cyclodesulfurative annulation reaction. New methodology for the preparation of guanosine and guanosine-type nucleoside analogsThe Journal of Organic Chemistry, 1986
- The syntheses of acycloformycins and 5-amino-3-(2-hydroxyethoxy)-methylpyrazolo[4,3-d]pyrimidin-7(6H)-one, an analogue of the antiviral acycloguanosineJournal of the Chemical Society, Perkin Transactions 1, 1985
- C-nucleoside studies. Part 18. The synthesis of C-Nucleoside analogues of the antiviral agent (S)-9-(2,3-Dihydroxypropyl)adenineJournal of the Chemical Society, Perkin Transactions 1, 1985
- Acyclo analogs of formycin aJournal of Heterocyclic Chemistry, 1984
- C-nucleoside studies. Part 17. The synthesis of 3(5)-carbamoyl-5(3)-β-Dribofuranosylpyrazole (4-deoxypyrazofurin) and 4-amino-3(5)-carbamoyl-5(3)-β-D-ribofuranosylpyrazoleJournal of the Chemical Society, Perkin Transactions 1, 1984
- Conversion of formycin into the fluorescent isoguanosine analogue 7-amino-3-(β-D-ribofuranosyl)-1H-pyrazolo[4,3-d]pyrimidin-5(4H)-oneJournal of the Chemical Society, Perkin Transactions 1, 1984
- Pyrazolopyrimidine nucleosides. 13. Synthesis of the novel C-nucleoside 5-amino-3-(.beta.-D-ribofuranosyl)pyrazolo[4,3-d]pyrimidin-7-one, a guanosine analog related to the nucleoside antibiotic formycin BJournal of the American Chemical Society, 1982
- C-Nucleoside studies. Part XI. Cine-substitution in 1,4-dinitropyrazoles; application to the synthesis of formycin via nitropyrazole derivativesCanadian Journal of Chemistry, 1980
- Cyclization of 5‐amino‐1‐β‐d‐ribofuranosylimidazole‐4‐carboxamide (AICA‐riboside): A reviewJournal of Heterocyclic Chemistry, 1978