Ce. Kerr et al., Synthesis of N,N-dialkylaniline-2 '-deoxyuridine conjugates for DNA-mediated electron transfer studies, NUCLEOS NUC, 19(5-6), 2000, pp. 851-866
Syntheses of two analogs of deoxyuridine with N,N-dialkylaniline chromophor
es are reported. 5-[3-(N-methylphenylamino)propanoyl]-2'-deoxyuridine (1) a
nd 5-[2-(4-N,N-dimethylaminophenyl)ethyl)]-2'-deoxyuridine (2) are prepared
by palladium-mediated coupling. Preparation of 2 was facilitated by in sit
u transient O-4-trimethylsiyl protection during alkynylation which suppress
ed secondary cyclization of the coupling adduct.