4-(1,2,4-Triazol-1-yl)- and 4-(3-nitro-1,2,4-triazol-1-yl)-1-(β-D-2,3,5-tri-O-acetylarabinofuranosyl)pyrimidin-2(1H)-ones. Valuable intermediates in the synthesis of derivatives of 1-(β-D-arabinofuranosyl)cytosine (ara-C)
- 1 January 1982
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 5,p. 1171-1176
- https://doi.org/10.1039/p19820001171
Abstract
Treatment of the acetylated derivative (3b), which was prepared from uridine in 86% overall yield, with tri(1H-1,2,4-triazol-1-yl)phosphine oxide gave compound (6a) in high yield, and with 3-nitro-1,2,4-triazole and diphenyl phosphorochloridate it gave compound (6b) in high yield. When the former product (6a) was allowed to react with ammonia, methylamine, dimethylamine, and morpholine at room temperature, and the products further deacetylated if necessary, ara-C (1; R1= R2= H) and its corresponding 4-N-alkyl derivatives (1; R1= H, R2= Me), (1; R1= R2= Me), and [1; R1,R2=–(CH2)2O(CH2)2–] were obtained in very high yields. 4-N-Phenyl-ara-C (1; R1= H, R2= Ph) was obtained in high yield when compound (6a) or (6b) was heated with aniline in pyridine solution and the products then deacetylated. The nitro-compound (6b) was converted into the ara-C derivative (1; R1= H, R2= CH2CO2Me), and the sulphide (7) was obtained following the deacetylation of the products of the reaction between the 1,2,4-triazolyl derivative (6a), toluene-p-thiol, and triethylamine.This publication has 2 references indexed in Scilit:
- Nucleosides. XLVII. Syntheses of some N4-substituted derivatives of 1-.beta.-D-arabinofuranosylcytosine and -5-fluorocytosineJournal of Medicinal Chemistry, 1968
- Nucleosides. XXIX. 1-β-D-Arabinofuranosyl-5-fluorocytosine and Related Arabino Nucleosides1Journal of Medicinal Chemistry, 1966