Facile and novel one-pot three-component synthesis of isatin-thiazoles catalyzed by biogenic iron oxide nanoparticles

Abstract

• Novel biogenic preparation of Fe 2 O 3 nanoparticles using Areca Nut extract mediated solution combustion method. • Characterization of prepared nanoparticles using X-RD, SEM with EDX, TGA, TEM, FT-IR and UV-Vis Spectroscopy. • Synthesis of some 3- [2-(5-phenyl-1, 3-thiazol-2-yl) hydrazinyl]-1, 3-dihydro-2H-indol-2-one derivatives by using biogenic nano Fe 2 O 3 as a catalyst. • Characterization of synthesized compounds by different spectral techniques like FT-IR, NMR and LCMS. • The DFT studies of synthesized compounds showed that the HOMO and LUMO plays very important role to know the structural activity relationship. • Docking and ADMET studies reveled that all the docked molecules exhibited good drug like properties. • All the studied compounds exhibited noteworthy pharmacological properties such as antimicrobial and antimycobacterial activity. • Catalyst was recyclable upto 6 th cycle with yield of 86% of products. This study presents the preparation of novel biogenic Fe 2 O 3 by solution combustion method and its characterization by X-ray diffraction, scanning electron microscopy, energy-dispersive X-ray spectroscopy, TGA, TEM, FT-IR and UV-Vis spectroscopy. Then the study of catalytic activity of Fe 2 O 3 nanoparticles in ethanol for one-pot synthesis of a library of isatin-thiazoles via three-component reaction of various isatin with thiosemicarbazide and different phenacyl bromides. The structure of the synthesized compounds 3-[2-(5-phenyl-1, 3-thiazol-2-yl) hydrazinyl]-1, 3-dihydro-2H-indol-2-one derivatives is confirmed by different spectroscopic studies. The advantages of this method include its broad substrate scope, clean reaction profile, short reaction times and high yields at low catalyst loading. Further, the product does not require any chromatographic purification and the method has the potential for large-scale applications in pharmaceutical industries. In addition, the developed catalyst can be recovered and reused 6 times without significant loss of activity.