Eco-Friendly One-Pot Synthesis of Tetrahydrobenzo[b]Pyran and Dihydropyrano[3,2-c]Chromene Derivatives Using Functionalized Fe₃O₄@SiO₂@SO₃H Under MWI.

Shekhanavar, Raju; Khatavi, Santosh; Kamanna, Kantharaju

The present work describes a greener method of preparation of Fe3O4 nanoparticles, which are then functionalized to Fe3O4@SiO2@SO3H, and employed in the one-pot three-component synthesis of tetrahydrobenzo[b]pyran and dihydropyrano[3,2-c]chromene derivatives. These synthesized derivatives are an important class of heterocyclic scaffolds and exhibit significant potential as anti-coagulant, diuretic, spasmolytic, anticancer, and anti-anaphylactic agents. The prepared MNP-based catalysts were characterized using XRD, FE-SEM, VSM, TG-DTA, and Raman spectroscopy. The synthesis of derivatives involved the condensation reaction of enolizable compounds with aldehyde, dimedone, and ethyl cyanoacetate for tetrahydrobenzo[b]pyran, and the reaction of aromatic aldehyde, 4-hydroxycoumarin, and malononitrile for dihydropyrano[3,2-c]chromene synthesis. The reaction was optimized using different techniques such as stirring, ultrasonication, and microwave irradiation, with microwave irradiation method demonstrating faster product separation and high yield. The homogeneity of the isolated product was analyzed by FT-IR,1H-13C-NMR, and mass spectrometry. The advantages of this method include its simplicity, eco-friendliness, cost-effectiveness, and it also evades the use of toxic metals and solvents. The product is easily isolated through a simple workup process and recrystallization using ethanol yields pure product isolation.

PYRAN; MAGNETIC nanoparticles; HEAVY metals; RAMAN spectroscopy; CONDENSATION reactions; PYRAN derivatives

Polycyclic Aromatic Compounds, 2025, Vol 45, Issue 1, p60

1040-6638

Academic Journal

10.1080/10406638.2024.2389939