Trimesic Acid-functionalized Chitosan: A Novel and Efficient Multifunctional Organocatalyst for Green Synthesis of Polyhydroquinolines and Acridinediones Under Mild Conditions

Trimesic acid-functionalized chitosan (Cs/ECH-TMA) material was prepared through a simple procedure by using inexpensive and commercially available chitosan (Cs), epichlorohydrin (ECH) linker and trimesic acid (TMA). The obtained bio-based Cs/ECH-TMA material was characterized using energy-dispersive X-ray (EDX) and Fourier-transform infrared (FTIR) spectroscopy, field emission scanning electron microscopy (FESEM) and X-ray diffraction (XRD) analysis. The Cs/ECH-TMA material was successfully used, as a multifunctional heterogeneous and sustainable catalyst, for efficient and expeditious synthesis of medicinally important polyhydroquinoline (PHQ) and polyhydroacridinedione (PHA) scaffolds through the Hantzsch condensation in a one-pot reaction. Indeed, the heterogeneous Cs/ECH-TMA material can be considered as a synergistic multifunctional organocatalyst due to the presence of a large number of acidic active sites in its structure as well as hydrophilicity. Both PHQs and PHAs were synthesized in the presence of biodegradable heterogeneous Cs/ECH-TMA catalytic system from their corresponding substrates in EtOH under reflux conditions and high to quantitative yields. The Cs/ECH-TMA catalyst is recyclable and can be reused at least four times without significant loss of its catalytic activity.