Nucleosides, XLVIII. Syntheses and Properties of Quinazoline N-1-Ribofuranosides

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.