Синтез и исследование гетероциклических аналогов BODIPY
Аннотация
Boracycles are cyclic compounds containing boron atoms in a cycle. Boron-containing heterocycles show unique electronic properties imparted by the electron-deficient three-coordinate boron center. These conjugated boracycles have found utility in various applications, including:
organic light-emitting diodes (OLEDs), medical imaging, anion sensing, field-effect transistors, and biological activities. The main objective of our research includes the synthesis of various boron-containing organic molecules. So, during our research, we were engaged in the synthesis of N,O-containing boracycles. For this purpose, the present work aims to synthesize 2-(2-hydroxyphenyl)–3H-quinazolin-4-ones and their BF2 complexes. We suggested two-step method based on the condensation of anthranilamide with benzaldehyde under room temperature and subsequent oxidation with copper chloride carried out at 80 ºC in ethanol for 2 h. Herein, we have applied the procedure to synthesize quinazolinone derivatives with different substituents in phenol ring, such as halogen like bromo groups. After successive synthesis of quinazolinone derivatives, all novel difluoroboron complexes have been prepared by the treatment of the quinazolinones with BF3.OEt2 in the mixture of toluene and glacial acetic acid under reflux. In addition, an efficient mechanochemical FeCl3 catalyzed ortho-hydroxyalkylation of phenols was also attempted with aldehydes promoted by phenyl boronic acid, leading to the formation of 2-aryl-1,3,2-aryldioxaborins. And, other organic molecules have also been prepared as Aza-BODIPY precursors.
organic light-emitting diodes (OLEDs), medical imaging, anion sensing, field-effect transistors, and biological activities. The main objective of our research includes the synthesis of various boron-containing organic molecules. So, during our research, we were engaged in the synthesis of N,O-containing boracycles. For this purpose, the present work aims to synthesize 2-(2-hydroxyphenyl)–3H-quinazolin-4-ones and their BF2 complexes. We suggested two-step method based on the condensation of anthranilamide with benzaldehyde under room temperature and subsequent oxidation with copper chloride carried out at 80 ºC in ethanol for 2 h. Herein, we have applied the procedure to synthesize quinazolinone derivatives with different substituents in phenol ring, such as halogen like bromo groups. After successive synthesis of quinazolinone derivatives, all novel difluoroboron complexes have been prepared by the treatment of the quinazolinones with BF3.OEt2 in the mixture of toluene and glacial acetic acid under reflux. In addition, an efficient mechanochemical FeCl3 catalyzed ortho-hydroxyalkylation of phenols was also attempted with aldehydes promoted by phenyl boronic acid, leading to the formation of 2-aryl-1,3,2-aryldioxaborins. And, other organic molecules have also been prepared as Aza-BODIPY precursors.