Benzimidazoazapurines: Design, Synthesis, and Photophysical Study.

Autor: Fedotov VV; Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002, Russia., Ulomsky EN; Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002, Russia., Belskaya NP; Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002, Russia., Eltyshev AK; Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002, Russia., Savateev KV; Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002, Russia., Voinkov EK; Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002, Russia., Lyapustin DN; Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002, Russia., Rusinov VL; Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002, Russia.
Jazyk: angličtina
Zdroj: The Journal of organic chemistry [J Org Chem] 2021 Jun 18; Vol. 86 (12), pp. 8319-8332. Date of Electronic Publication: 2021 Jun 07.
DOI: 10.1021/acs.joc.1c00760
Abstrakt: 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.
Databáze: MEDLINE