One-pot three-component synthesis of Acridine derivatives in glycerin media

A plenty of natural and synthetic materials including the acridine skeleton display interesting biological and physical activities, such as antimalaria and antitumor agents, and multihydroacridineone derivatives have been reported to have high fluorescence efficiency and can be used as fluorescent molecular probes for monitoring of polymerization process [1-3]. In this project, naphthylamine, dimedone and aryl aldehydes compounds in glycerin media was stirred at room temperature. TLC indicated completion of the reaction. After completion of the reaction, water was added and the product was appeared as a solid compound. After filtration, the desired product was dried and recrystallized for more purification by ethanol and identified by Perkin Elmer FT-IR spectrometer and 1H-NMR spectra on Bruker DRX- 300 MHZ NMR instrument. The condensation reaction between 1-naphthyl amine, dimedone and aryl aldehydes was promoted in glycerin media at ambient temperature to afford 7-aryl-7,10,11,12-tetrahydrobenzo[c]acridin-8(9H)-one derivatives (Scheme 1). To study the scope of the reaction, a series of aryl aldehydes carrying electron donating and electron withdrawing groups were subjected to produce their corresponding acridin-8(9H)-one derivatives in high yields. This method gives remarkable advantages such as simple work-up procedure, using of the green and inexpensive procedure with excellent yields.