Eco-Friendly One-Pot Synthesis of Tetrahydrobenzo[ <i>b</i> ]Pyran and Dihydropyrano[3,2- <i>c</i> ]Chromene Derivatives Using Functionalized Fe <sub>3</sub> O <sub>4</sub> @SiO <sub>2</sub> @SO <sub>3</sub> H Under MWI

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.

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Publication Details

Journal
Polycyclic aromatic compounds
Published
2024-08-23
DOI
https://doi.org/10.1080/10406638.2024.2389939
Citations
3
Primary Topic
Multicomponent Synthesis of Heterocycles
Type
article
Field-Weighted Citation Impact
0.75
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article

Eco-Friendly One-Pot Synthesis of Tetrahydrobenzo[ b ]Pyran and Dihydropyrano[3,2- c ]Chromene Derivatives Using Functionalized Fe 3 O 4 @SiO 2 @SO 3 H Under MWI

Raju Shekhanavar, Kantharaju Kamanna, Santosh Y. Khatavi
3 citations
Polycyclic aromatic compounds
Multicomponent Synthesis of Heterocycles
0.75
article

Eco-Friendly One-Pot Synthesis of Tetrahydrobenzo[ b ]Pyran and Dihydropyrano[3,2- c ]Chromene Derivatives Using Functionalized Fe 3 O 4 @SiO 2 @SO 3 H Under MWI

Raju Shekhanavar, Kantharaju Kamanna, Santosh Y. Khatavi
article en
3 citations

Abstract

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.

Polycyclic aromatic compoundsVol. 45(1)
Rani Channamma University, Belagavi (IN)
Responsible consumption and production
Openalex Percentile: Top 33%
Multicomponent Synthesis of Heterocycles
0.75
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Eco-Friendly One-Pot Synthesis of Tetrahydrobenzo[ <i>b</i> ]Pyran and Dihydropyrano[3,2- <i>c</i> ]Chromene Derivatives Using Functionalized Fe <sub>3</sub> O <sub>4</sub> @SiO <sub>2</sub> @SO <sub>3</sub> H Under MWI — Raju Shekhanavar, Kantharaju Kamanna, et al. · Polycyclic aromatic compounds (2024) | TGRS Research Map | TGRS