Synthesis and Characterization of New 8-trifluloromethyl Quinazolin-2,4-(3H)-Dione Nucleosides

Abstract

Synthesis of 8-trifluloromethyl quinazolin-2,4-(1H,3H)-dione 2. which have been ribosylated by coupling with 1-O-acetyl-2,3,5-tri-O-benzoyl--D-ribofuranose 4 by using the silylation method, afforded mixture -and -anomeric of the benzoylated nucleoside derivatives 5 and 6, respectively. Debenzoylation of each of 5 and 6 by sodium metal in dry methanol to afford the corresponding free nucleosides 7 and 8 respectively. The structures of the newly synthesis compounds have been confirmed on the basis of elemental analyses, IR, 1 HNMR, 13 CNMR and Mass spectral data.

Synthesis New of Nucleoside of 1,3-bis-(2,3,5-tri-O-Benzoyl-β-D-Ribofuranosyl)-8-(Trifluoromethyl)-2-Methyl-4-Quinazolinone

“…For the observation of CF3 groups, coupling constants for protons of the ribose moiety of an atom on N1 suggests this could be a cancellation of through-space and through-bond couplings. Meanwhile the protons' ribose moiety on N3 decoupling was not affected by 19 F. The proton's two glycoside bonds on N1 and N3 produced doublet signals at δ6.69 (d, 1H, 3 JH-H = 5.1 Hz) H1'' and 5.69-5.63 (d,1H; 3 JH-H = 4.25 Hz) H1' for compound 6, which confirmed the β-anomeric configuration [4][5][6][7].…”