ZnCl<sub>2</sub>/Urea as a Deep Eutectic Solvent for the Preparation of Bis(indolyl)methanes Under Ultrasonic Conditions

Seyedi, Neda; Khabazzadeh, Hojatollah; Saeednia, Samira

doi:10.1080/15533174.2013.862828

Cited by 29 publications

(10 citation statements)

References 16 publications

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“…Notwithstanding the surge of interest in the use of DES in organic synthesis, currently only a few papers have had as the main subject the study of the combined action of DES and US irradiation. − This could prove fruitful for a reaction of industrial interest like DAr.…”

Section: Resultsmentioning

confidence: 99%

A Joint Action of Deep Eutectic Solvents and Ultrasound to Promote Diels–Alder Reaction in a Sustainable Way

Marullo

Meli

D’Anna

2020

ACS Sustainable Chem. Eng.

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The need to reduce environmental impact of chemical processes has induced a surge of attention in the choice of solvent and methodologies to carry them out. In this context, we studied the Diels–Alder reaction using N-ethylmaleimide as dienophile and changing the nature of the diene in deep eutectic solvents (DES) under both conventional heating and ultrasonic activation. DES obtained by the combination of different hydrogen bond acceptors and donors allowed assessing the role played by solvent nature. DES proved suitable solvent media for the target reaction, allowing higher yields and faster reactions compared to conventional organic solvents. The trend of yields, both in silent and under ultrasound irradiation, was rationalized considering solvent viscosity and structural organization. In particular, thanks to a combined approach of resonance light scattering (RLS) and 1H NMR investigation, a relationship between performance of the reaction and thickness and strength of the hydrogen bond network of the solvent was identified. Moreover, DES could be recycled up to eight times without any loss in yield. Using ultrasonic activation in combination with DES proved beneficial providing good yields in drastically reduced reaction times. From the standpoint of Green Chemistry, the combined use of ultrasound and DES allowed reducing energy consumption by more than 99% compared with silent reactions and proved beneficial for the scalability of the process.

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Section: Resultsmentioning

confidence: 99%

A Joint Action of Deep Eutectic Solvents and Ultrasound to Promote Diels–Alder Reaction in a Sustainable Way

Marullo

Meli

D’Anna

2020

ACS Sustainable Chem. Eng.

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“…In 2015, Seyedi et al. reported the preparation of DES by ZnCl 2 and urea . In the same year, Gano et al.…”

Section: Deep Eutectic Solventsmentioning

confidence: 99%

“…In 2011, Choiet et al reported 30 combinations with ChCl, natural carboxylic acids, different sugars, and even water, which formed viscous liquids, which they called "natural deep eutectic solvents" (NADESs) [17]. In 2015, Seyedi et al reported the preparation of DES by ZnCl 2 and urea [10]. In the same year, Gano et al reported the formation of FeCl 3 -based DES and FeCl3-based DES and their use in the extractive desulfurization of liquid fuel [11].…”

Section: Deep Eutectic Solvents 21 Preparation Of Deep Eutectic Solvmentioning

confidence: 99%

“…Recently, an increasing number of different compounds have been used in the preparation of DES as an HBA, such as an inorganic salt (ZnCl 2 and FeCl 3 ) and organics (betaine, glucose, citric acid etc.) . From 2003, the first DES was obtained at 80°C and stirred until a homogeneous liquid formed, and this synthetic method was then applied in the preparation of DESs .…”

Section: Deep Eutectic Solventsmentioning

confidence: 99%

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Development of deep eutectic solvents applied in extraction and separation

Row

2016

J of Separation Science

362

158

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Deep eutectic solvents, as an alternative to ionic liquids, have greener credentials than ionic liquids, and have attracted considerable attention in related chemical research. Deep eutectic solvents have attracted increasing attention in chemistry for the extraction and separation of various target compounds from natural products. This review highlights the preparation of deep eutectic solvents, unique properties of deep eutectic solvents, and synthesis of deep-eutectic-solvent-based materials. On the other hand, application in the extraction and separation of deep eutectic solvents is also included in this report. In this paper, the available data and references in this field are reviewed to summarize the applications and developments of deep eutectic solvents. Based on the development of deep eutectic solvents, an exploitation of new deep eutectic solvents and deep eutectic solvents-based materials is expected to diversify into extraction and separation.

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“…found in the literature regarding its uses, which include the electrodeposition of Zn-Ti alloys, 32 lignin modification, 33 the preparation of bis(indolyl)methanes, 34 and the electrochemical fabrication of nanoporous gold electrodes. 35 The remarkable importance of imidazoles together with the growing use of DESs in organic synthesis prompted us to develop a sustainable methodology for the synthesis of valuable organic compounds, and here we report the synthesis of imidazole derivatives by employing the urea-ZnCl 2 DES as an efficient, ecofriendly, and recyclable reaction medium.…”

Section: Syn Lettmentioning

confidence: 99%

Urea–Zinc Chloride Eutectic Mixture-Mediated One-Pot Synthesis of Imidazoles: Efficient and Ecofriendly Access to Trifenagrel

Higuera¹,

Peña-Solórzano²,

Ochoa‐Puentes³

2018

Synlett

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The low-melting mixture urea–ZnCl2 was evaluated as a novel reaction medium for the synthesis of imidazoles. The reaction between a dicarbonyl compound, ammonium acetate, and an aromatic aldehyde is efficiently catalyzed by the eutectic solvent, yielding a wide variety of triaryl-1H-imidazoles or 2-aryl-1H-phenanthro[9,10-d]imidazoles in good to excellent yields. In addition, the eutectic solvent was reused in five cycles without loss of its catalytic activity. This protocol was further explored for the synthesis of the drug trifenagrel, giving an excellent yield.

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ZnCl₂/Urea as a Deep Eutectic Solvent for the Preparation of Bis(indolyl)methanes Under Ultrasonic Conditions

Cited by 29 publications

References 16 publications

A Joint Action of Deep Eutectic Solvents and Ultrasound to Promote Diels–Alder Reaction in a Sustainable Way

A Joint Action of Deep Eutectic Solvents and Ultrasound to Promote Diels–Alder Reaction in a Sustainable Way

Development of deep eutectic solvents applied in extraction and separation

Urea–Zinc Chloride Eutectic Mixture-Mediated One-Pot Synthesis of Imidazoles: Efficient and Ecofriendly Access to Trifenagrel

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ZnCl2/Urea as a Deep Eutectic Solvent for the Preparation of Bis(indolyl)methanes Under Ultrasonic Conditions

Cited by 29 publications

References 16 publications

A Joint Action of Deep Eutectic Solvents and Ultrasound to Promote Diels–Alder Reaction in a Sustainable Way

A Joint Action of Deep Eutectic Solvents and Ultrasound to Promote Diels–Alder Reaction in a Sustainable Way

Development of deep eutectic solvents applied in extraction and separation

Urea–Zinc Chloride Eutectic Mixture-Mediated One-Pot Synthesis of Imidazoles: Efficient and Ecofriendly Access to Trifenagrel

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ZnCl₂/Urea as a Deep Eutectic Solvent for the Preparation of Bis(indolyl)methanes Under Ultrasonic Conditions