Nucleosides, XLVIII. Syntheses and Properties of Quinazoline N-1-Ribofuranosides
- 1 June 1991
- journal article
- research article
- Published by Taylor & Francis in Nucleosides and Nucleotides
- Vol. 10 (4) , 799-817
- https://doi.org/10.1080/07328319108046663
Abstract
Several 6- and 7-substituted quinazoline-2, 4-(1H, 3H)-diones (1–7) have been ribosylated with 1-0-acetyl-–2, 3, 5-tri-0-benzoyl-β-D-ribofuranose (8)via the “silyl”-method and Lewis acid catalysis in a highly regioselective manner to give the corresponding protected N-1 ribosides 9–15. Debenzoylation to the free nucleosides 16–22 was achieved by sodium methoxide. Thiation of 9–15 by Lawesson's reagent effected the conversion of the 4-oxo into the 4-thioxo function (23–29). Removal of the sugar protecting groups in these derivatives worked best with potassium carbonate in anhydrous MeOH to form in high yields 30–35. Treatment of the peracylated 4-thioxo quinazoline nucleosides with methanolic ammonia resulted in deacylation of the sugar moiety and in displacement of the sulfur function to give the corresponding 4-amino-1-β-D-ribofuranosylquinazolin-2(1H)-ones 36–41. The newly synthesized, nucleosides have been characterized by elemental analysis, UV- and 1H-NMR-spectra.Keywords
This publication has 22 references indexed in Scilit:
- Nucleosides, XLVII. Syntheses, Reactions and Properties of 6- and 7-p-Bromophenyllumazine N-1-NucleosidesPteridines, 1990
- Nucleosides, XLVI1Syntheses and Reactions of 6- and 7-p-Chlorophenyllumazine NucleosidesNucleosides, Nucleotides and Nucleic Acids, 1989
- Potent and selective anti-HTLV-IIILAV activity of 2′,3′-dideoxycytidinene, the 2′,3′-unsaturated derivative of 2′,3′-dideoxycytidineBiochemical and Biophysical Research Communications, 1986
- Reaction des glycosyl isonitriles avec les amines et les alcoolsCanadian Journal of Chemistry, 1981
- A novel one-step synthesis of thioquinazoline glycosides and pyrazolopyrimidine glycoside analogs.CHEMICAL & PHARMACEUTICAL BULLETIN, 1979
- Société Belge De Biochimie Belgische Vereniging Voor Biochemie: 107' Reunion, Liege, 16 Décembre 1978Archives Internationales de Physiologie et de Biochimie, 1979
- Polyazanaphthylene nucleosides II. Synthesis of β‐D‐ribofuranosyl derivatives of 4‐quinazoloneJournal of Heterocyclic Chemistry, 1969
- Antiviral activity of certain substituted purine and pyrimidine nucleosidesCellular and Molecular Life Sciences, 1969
- Neuere Methoden der präparativen organischen Chemie IV. Die Silylierung als Hilfsmittel in der organischen SyntheseAngewandte Chemie, 1965
- Über die Verseifung acetylierter KohlenhydrateBerichte der deutschen chemischen Gesellschaft (A and B Series), 1936