Synthesis and investigation on optical and electrochemical properties of 2,4-diaryl-9-chloro-5,6,7,8-tetrahydroacridines

Abstract

A facile synthesis of 2,4-diaryl-9-chloro-5,6,7,8-tetrahydroacridine derivatives is reported which is based on POCl3-mediated cyclodehydration followed by double Suzuki–Miyaura cross-coupling. The absorption and fluorescence properties of the obtained products were investigated and their HOMO/LUMO energy levels were estimated by cyclic voltammetry measurements. Besides, density functional theory calculations were carried out for further exploration of their electronic properties.

Cross-Coupling Reactions of Polyhalogenated Heterocycles

“…73 The Suzuki–Miyaura reaction of 209 with two equivalents of arylboronic acids, carried out by Najeh Tka (a postdoctoral fellow from Monastir in Tunisia), afforded 2,4-diaryl-9-chloro-5,6,7,8-tetrahydroacridines 210a – i in moderate to excellent yields (Figure 43 ). 74 The Sonogashira reaction of 209 with two equivalents of alkynes gave 2,4-dialkynyl-9-chloro-5,6,7,8-tetrahydroacridines 211a – g in good to excellent yields. 75 The regioselectivity can be explained by the better leaving group ability of bromide as compared to chloride, despite the effect that the chloride is located in a rather activated position in the pyridine moiety.…”

Metal-free synthesis of functionalized tacrine derivatives and their evaluation for acetyl/butyrylcholinesterase and α-glucosidase inhibition

“…4 Beyond their biological activities, these acridines have garnered significant attention in recent years in the area of materials science because of their promising photophysical and electrochemical characteristics as organic electronic devices and organic light-emitting diodes. 5…”