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New approach to unsymmetrical 1,3-diazatriphenylenes through intramolecular oxidative cyclodehydrogenation

Author:
Verbitskiy, Egor V., Eltsov, Oleg S., Zhilina, Ekaterina F., Pakhomov, Ilya M., Rusinov, Gennady L., Chupakhin, Oleg N., Charushin, Valery N.
Source:
Tetrahedron 2019 v.75 no.18 pp. 2687-2696
ISSN:
0040-4020
Subject:
chemical reactions, chemical structure, pyrimidines
Abstract:
An efficient synthetic route towards previously inaccessible dibenzo[f,h]quinazolines and [1]benzothieno[3,2-f]benzo[h]quinazolines through FeCl3-mediated intramolecular oxidative cyclodehydrogenation of readily available 5-([1,1′-biphenyl]-2-yl)pyrimidines and 5-(2-phenylbenzo[b]thiophen-3-yl)pyrimidines is described. Molecular orbital calculations (DFT), as well as redox and photophysical measurements for all new compounds have been performed. The data show that the reported polycyclic systems have a potential to use in organic electronic applications.
Agid:
6357928