One-pot Multicomponent Synthesis of pyrrolo[1,2-d][1,4]benzoxazines and pyrrolo[1, 2-a]pyrazines in Water Catalyzed by Fe3O4@SiO2@L-Arginine-SA Magnetic Nanoparticles

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Author(s): Hedieh Rostami, Lotfi Shiri*

Journal Name: Current Organic Synthesis

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Abstract:

Aims: Synthesis of pyrrolo[1,2-d][1,4]benzoxazines and pyrrolo[1,2-a]pyrazines using magnetic nanoparticles.

Background: One-pot, three component reaction for the synthesis of pyrrolo[1,2- d][1,4]benzoxazines and pyrrolo[1,2-a]pyrazines reported. For the synthesis of pyrrolo[1,2- d][1,4]benzoxazines used of 2-aminophenols, dialkylacetylenedicarboxylates and β-nitrostyrene derivatives and Pyrrolo[1,2-a]pyrazines synthesized from reaction of ethylenediamine, dialkylacetylenedicarboxylates and β-nitrostyrene derivatives.

Objective: Cosidering the importance of heterocycle compounds, we report an efficient procedure for the synthesis of pyrrolo[1,2-d][1,4]benzoxazines and pyrrolo[1,2-a]pyrazines in water by Fe3O4@SiO2@L-Arginine-SA magnetic nanoparticles.

Methods: 2-aminophenol (0.5 mmol) and dimethylacetylenedicarboxylate (0.5 mmol) in water (3 ml) were stirred at room temperature for 10 min. Then, β-nitrostyrene (0.5 mmol) and Fe3O4@SiO2@L-Arginine-SA MNPs (0.07 g) were added and the mixture reflux for 5 h. After completion of the reaction, the mixture was cooled to room temperature and catalyst was separated with external magnet and product extracted with dichloromethane. More purification of products was performed by column chromatography (n-hexane/ethyl acetate 4:1). Ethylenediamine (0.6 mmol) was added to dialkylacetylenedicarboxylate (0.6 mmol) in 3 ml water and was stirred for 10 min at room temperature. After, β-nitrostyrene (0.5 mmol) and Fe3O4@SiO2@L-Arginine-SA MNPs (0.06 g) were added to mixture reaction and reflux for 3 h. After completion, the mixture reaction was cooled to room temperature and catalyst was separated by an external magnet. Then, product was extracted with dichloromethane. For more purification used column chromatography (n-hexan/ ethylacetate 1:1).

Result: In this research, we are synthesised new derivatives of pyrrolo[1,2-d][1.4]benzoxazines and pyrrolo[1,2-a]pyrazines in green conditions consist of use of water as a green solvent and magnetic nanoparticles.

Conclusion: In this research, we are synthesised new derivatives of pyrrolo[1,2- d][1.4]benzoxazines and pyrrolo[1,2-a]pyrazines in green conditions consist of use of water as a green solvent and magnetic nanoparticles which easily separated from mixture with an external magnet and have capability recovery and reusability. Also, in this work, yield is good and time of reactions is low in compared with prior research.

Other: Use of water as a green solvent.

Keywords: Three component reaction Pyrrolo[1, 2-d][1, 4]benzoxazines, Pyrrolo[1, 2-a]pyrazines, β-Nitrostyrene derivatives, Nanoparticles, scanning electron microscopy.

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(E-pub Ahead of Print)
DOI: 10.2174/1573409916666200128163047
Price: $95

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