Ol. Acevedo et al., SYNTHESIS OF C-4 SUBSTITUTED PYRIMIDINE NUCLEOSIDE ANALOGS - PREPARATION OF SEVERAL 4-(2-OXOALKYLIDENE)-2(1H)-PYRIMIDINONE RIBONUCLEOSIDES, Journal of heterocyclic chemistry, 31(4), 1994, pp. 989-995
A series of 4-(1-alkynyl)-2(1H)-pyrimidinone ribonucleosides were synt
hesized from the Pd-catalyzed coupling of terminal alkynes to the 4-ch
loropyrimidin-2-one ribonucleoside (2). These compounds were hydrated,
using three different methods, to afford the 4-(2-oxoalkylidene)-2(1H
)-pyrimidinones. The 4-enol-pyrimidin-2-one structure of the title com
pounds offers functional groups with the potential for Watson-Crick hy
drogen bonding.