A highly
efficient approach to a new class of polycyclic 8-azapurines,
benzo[4,5]imidazo[1,2-a][1,2,3]triazolo[4,5-e]pyrimidines (BITPs), with good photophysical characteristics
is proposed. The approach comprises condensation of aminobenzimidazoles
with 3-oxo-2-phenylazopropionitrile to form 3-(arylazo)benzo[4,5]imidazo[1,2-a]pyrimidine-4-amines, which undergo oxidative cyclization
by the catalytic action of copper(II) acetate, resulting in BITPs
with 73–84% yield. Spectral investigations demonstrated the
fluorescent properties of BITPs, exhibiting good quantum yields (up
to 60%) with maxima absorption at 379–399 and emission at 471–505
nm.