Abstract
A simple, high yielding synthesis leading to the functionalization of some pyrimidine bases with a 1,6-heptadienyl moiety spaced from the
N
−
1 position by a methylene group is described. A key step in this synthesis involves a Mitsunobu reaction by coupling
3
N-benzoyluracil and
3
N-benzoylthymine to 2-allyl-pent-4-en-1-ol followed by alkaline hydrolysis of the
3
N-benzoyl protecting groups. This protocol should eventually lend itself to the synthesis of a host of
N-alkylated nucleoside analogs.
The absorption and emission properties of these pyrimidine derivatives (
3–
6) were studied in solvents of different physical properties. Computerized analysis and multiple regression techniques were applied to calculate the regression and correlation coefficients based on the equation that relates peak position
λ
max to the solvent parameters that depend on the H-bonding ability, refractive index, and dielectric constant of solvents.