Msp. Sarma et al., SYNTHESIS OF QUINAZOLINE C-NUCLEOSIDES - A NEW CLASS OF 6 6 BICYCLIC PURINE-LIKE ANALOGS/, Nucleosides & nucleotides, 14(3-5), 1995, pp. 397-400
The quinazoline C-nucleoside congeners of adenosine (1) and inosine (2
) have been obtained by radical-induced addition of 4-bromobulyronitri
le to C-ribosyl acrylonitrile 10. A base-catalyzed Ziegler-Thorpe cycl
ization of the dinitrile thus obtained (II) followed by aromatization
with DDQ afforded key intermediate 6-ribosylated anthranilonitrile 14
and its alpha-isomer. Annulation of a pyrimidine ring onto 14 or onto
the corresponding o-amino-amide followed by deblocking with MeOH/HCl f
inally gave 1 or 2 respectively.