Fedotov Victor V, Ulomsky Evgeny N, Belskaya Nataliya P, Eltyshev Alexander K, Savateev Konstantin V, Voinkov Egor K, Lyapustin Daniil N, Rusinov Vladimir L
Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002, Russia.
J Org Chem. 2021 Jun 18;86(12):8319-8332. doi: 10.1021/acs.joc.1c00760. Epub 2021 Jun 7.
A highly efficient approach to a new class of polycyclic 8-azapurines, benzo[4,5]imidazo[1,2-][1,2,3]triazolo[4,5-]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-]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.
提出了一种高效合成新型多环8-氮杂嘌呤——苯并[4,5]咪唑并[1,2 - ][1,2,3]三唑并[4,5 - ]嘧啶（BITP）的方法，该方法具有良好的光物理特性。该方法包括氨基苯并咪唑与3-氧代-2-苯基偶氮丙腈缩合形成3-（芳基偶氮）苯并[4,5]咪唑并[1,2 - ]嘧啶-4-胺，其在醋酸铜（II）的催化作用下进行氧化环化，得到产率为73 - 84%的BITP。光谱研究表明BITP具有荧光特性，量子产率高达60%，最大吸收波长在379 - 399nm，发射波长在471 - 505nm。
