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 is reported. For the synthesis of pyrrolo[1,2-d][1,4]benzoxazines use of 2-
aminophenols, dialkylacetylenedicarboxylates and β -nitrostyrene derivatives and Pyrrolo[1,2-a]pyrazines
synthesized from reaction of ethylenediamine, dialkylacetylenedicarboxylates and β-nitrostyrene derivatives is
discussed.
Materials and 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@LArginine-
SA MNPs (0.07 g) were added and the mixture was refluxed for 5 h. After completion of the reaction,
the mixture was cooled to room temperature and the catalyst was separated with external magnet and product
extracted with dichloromethane. More purification of products was performed by column chromatography (nhexane/
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. Later, β -nitrostyrene (0.5 mmol) and
Fe3O4@SiO2@L-Arginine-SA MNPs (0.06 g) were added to mixture reaction and refluxed for 3 h. After
completion, the mixture reaction was cooled to room temperature and the catalyst was separated by an external
magnet. Then, the product was extracted with dichloromethane. For more purification column chromatography
was used (n-hexane/ethylacetate 1:1).
Results and Discussion:
In this research, we have synthesized new derivatives of pyrrolo[1,2-
d][1.4]benzoxazines and pyrrolo[1,2-a]pyrazines in green conditions consisting of use of water as a green
solvent and magnetic nanoparticles.
Conclusion:
In this research, we have synthesized new derivatives of pyrrolo[1,2-d][1.4]benzoxazines and
pyrrolo[1,2-a]pyrazines in green conditions consisting of use of water as a green solvent and magnetic
nanoparticles which were easily separated from mixture with an external magnet and had the capability to be
recovered and reused. Also, in this work, the yield was good and the time of reactions was low compared with
prior research.
Clean one-pot multicomponent synthesis of pyrans using a green and magnetically recyclable heterogeneous nanocatalyst