TiO2 NPs-Coated Carbone Nanotubes as a Green and Efficient Catalyst for the Synthesis of [1]Benzopyrano[b][1]benzopyranones and Xanthenols in Water

Abstract

Aim and Objective: Results of pharmacological studies have revealed that chromenes (2H-1-benzopyran derivatives) and xanthenes (dibenzopyrans) constitute major classes of heterocyclic compounds, due to their useful biological activities. Moreover, during the last decade, the use of metal oxide nanoparticles (NPs) as heterogeneous catalysts has been extensively studied due to their high physical and chemical abilities. The aim of the ongoing research was to prove the catalytic efficiency of the synthesized TiO2 NPs supported by carbon nanotubes (TiO2-CNTs) for the preparation of these heterocyclic scaffolds. Materials and Methods: The present work is focused on a green and efficient synthesis of [1]benzopyrano[b][1]benzopyran-6-ones and xanthenols via a pseudo three-component reaction of salicylaldehydes with active methylene compounds including 4-hydroxycoumarin (4-hydroxy-2H-1- benzopyran-2-one) or 3,4-methylenedioxyphenol, in a molar ratio of 1:2. The reaction was carried out in the presence of the synthesized TiO2-CNTs as a catalyst in aqueous media at room temperature. The synthesized catalyst was fully characterized by the scanning electron microscopy (SEM), the transmission electron microscopy (TEM), the powder X-ray diffraction (XRD), and the energy dispersive X-ray detector (EDX) techniques. All the synthesized compounds were characterized by IR, 1H and 13C NMR spectroscopy, as well as elemental analyses. Results: Sixteen target compounds containing [1]benzopyrano[b][1]benzopyran-6-ones and xanthenols were successfully synthesized in high yields (92-98%) within short reaction times (1.5-3 h). Conclusion: In this research, TiO2-CNTs were used as an efficient recyclable catalyst for the synthesis of [1]benzopyrano[b][1]benzopyran-6-ones and xanthenols by the pseudo three-component reaction of salicylaldehydes with active methylene compounds including 4-hydroxycoumarin (4- hydroxy-2H-1-benzopyran-2-one) or 3,4-methylenedioxyphenol. The introduced method is mild, environmentally benign and effective to give the products in high yields and in short reaction times.