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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
Current Organic Synthesis ( IF 1.7 ) Pub Date : 2020-08-31 , DOI: 10.2174/1573409916666200128163047
Hedieh Rostami 1 , Lotfi Shiri 1
Affiliation  

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 Discussions: 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.



中文翻译:

Fe3O4 @ SiO2 @ L-精氨酸-SA磁性纳米粒子催化水中单锅多组分合成吡咯并[1,2-d] [1,4]苯并恶嗪和吡咯并[1,2-a]吡嗪

目的:利用磁性纳米粒子合成吡咯并[1,2-d] [1,4]苯并恶嗪和吡咯并[1,2-a]吡嗪。

背景:报道了用于合成吡咯并[1,2-d] [1,4]苯并恶嗪和吡咯并[1,2-a]吡嗪的一锅三组分反应。对于吡咯并[1,2-d] [1,4]苯并恶嗪的合成,使用2-氨基苯酚,二烷基乙酰二羧酸酯和β-硝基苯乙烯衍生物以及由乙二胺,二烷基乙酰二羧酸酯和β-的反应合成的吡咯并[1,2-a]吡嗪讨论了硝基苯乙烯衍生物。

材料与方法:在室温下将2-氨基苯酚(0.5 mmol)和乙酰基二羧酸二甲酯(0.5 mmol)于水(3 ml)中搅拌10分钟。然后,添加β-硝基苯乙烯(0.5 mmol)和Fe3O4 @ SiO2 @ Larginine-SA MNP(0.07 g),并将混合物回流5小时。反应完成后,将混合物冷却至室温,并用外部磁体分离催化剂,并用二氯甲烷萃取产物。通过柱色谱法(正己烷/乙酸乙酯4:1)进行产物的更多纯化。将乙二胺(0.6 mmol)添加到3 ml水中的乙炔基二羧酸二烷基酯(0.6 mmol)中,并在室温下搅拌10分钟。然后,将β-硝基苯乙烯(0.5 mmol)和Fe3O4 @ SiO2 @ L-精氨酸-SA MNPs(0.06 g)加入到混合物反应中并回流3小时。完成后,将混合物反应冷却至室温,并通过外部磁体分离催化剂。然后,产物用二氯甲烷萃取。为了进一步纯化,使用柱色谱法(正己烷/乙酸乙酯1∶1)。

结果与讨论:在这项研究中,我们合成了吡咯并[1,2- d] [1.4]苯并恶嗪和吡咯并[1,2-a]吡嗪的新衍生物,包括水作为绿色溶剂和磁性纳米粒子。

结论:在这项研究中,我们合成了吡咯并[1,2-d] [1.4]苯并恶嗪和吡咯并[1,2-a]吡嗪的新衍生物,包括水作为绿色溶剂和磁性纳米粒子。可以很容易地通过外部磁铁将其与混合物分离,并具有回收和再利用的能力。而且,在这项工作中,与先前的研究相比,收率好并且反应时间短。

更新日期:2020-09-25
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