A novel heterogeneous acid–base nano-catalyst designed based on graphene oxide for synthesis of spiro-indoline-pyranochromene derivatives

Abstract

Abstract Nano graphene oxide/3-aminopyridine has been introduced as a new, efficient and robust heterogeneous organic catalyst for synthesis of spiro-indoline-pyranochromene derivatives. Nano graphene oxide/3-aminopyridine was provided in an easy and green way from GO. Firstly, graphene oxide (GO) was synthesized and then 3-aminopyridine was immobilized with covalent bonds on its surface as a nitrogenous organic compound, in this step we didn’t use any organic or toxic substance. This bonding was easily performed due to the presence and reactivity of the epoxy groups in the GO structure. Because of its vast-surface nano-layers, GO could be effective in appropriate dispersion of 3-aminopyridine on its surface and increasing the catalyst performance. The new catalyst was analysed using different microscopic and spectroscopic techniques such as Fourier-transform infrared (FT-IR), field emission scanning electron microscope (SEM), energy-dispersive X-ray spectroscopy (EDS), X-ray diffraction (XRD) and thermogravimetric analysis (TGA). Our results showed that the distance between GO plates was increased in the presence of the modifying agent. This is due to the placement of the organic compound between the GO sheets. Finally, the ability of our new nano-catalyst in the synthesis of some spiro-indoline-pyranochromene and dihydropyranochromene derivatives was evaluated and acceptable results were obtained. Eight analogous of spiro-indoline-pyranochromene (4a-4 h) were synthesized in high yields and characterized. Using 3-aminopyridine as an organic and efficient catalyst, its stabilization by a simple method on GO, recycling of the catalyst up to 7 times and obtaining a highly pure product were the points that made the present work more attractive. Graphical Abstract

Keywords

• Graphene oxide
• Organocatalyst
• 3-Aminopyridine