Chemoselective synthesis of xanthenes and tetraketones in a choline chloride-based deep eutectic solvent

Azizi, Najmedin; Dezfooli, Sahar; Hashemi, Mahmoud Reza

doi:10.1016/j.crci.2013.05.002

Cited by 56 publications

(29 citation statements)

References 35 publications

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“…The best combination was with zinc chloride (ChCl-ZnCl2, 1:2 molar ratio), producing a reaction medium that catalysed the condensation reaction of aromatic aldehydes with 1,3-cyclohexanediones (Scheme 8). [59] The same transformation was also reported in a mixture of N,N'-dimethylurea and citric acid (3:2 mass ratio, Scheme 8). For the latest, recyclability was studied observing a small loss of activity after 6 cycles.…”

Section: Condensation-mediated Processesmentioning

confidence: 76%

Deep Eutectic Solvents: The Organic Reaction Medium of the Century

et al. 2016

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This microreview summarizes the use of deep eutectic solvents (DES) and related melts in Organic Synthesis. This type of solvents combine the great advantages of other proposed environmentally benign alternative solvents, such as low toxicity, high availability, low inflammability, high recyclability, low volatility and low price, avoiding many disadvantages of these neoteric media. The fact that many of the components of the mixture come directly from Nature assures their biodegradability and renewability. The classification and distribution of the reactions in different sections along this microreview, as well as the emphasis paid to their scope, easily allows a general reader to understand the actual state of art, and the great opportunities opened, not only for academic proposes but also for industry.

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Section: Condensation-mediated Processesmentioning

confidence: 76%

Deep Eutectic Solvents: The Organic Reaction Medium of the Century

et al. 2016

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“…Analogously, the same group evaluated different ChCl‐based DES to be used as catalysts in the synthesis of xanthenes and tetraketones by means of tandem Knoevenagel condensation and Michael addition reactions . In these cases, the reaction consisted of a high loading of a mixture of an aldehyde (0.53 kg L −1 ) and dimedone (0.14 kg L −1 ) in DES heated at 80 °C under stirring for 2–6 h. With 1:2 ChCl/urea (molar ratio) DES, tetraketones were obtained selectively as the only product, whereas for the 1:2 ChCl/ZnCl 2 (molar ratio) DES, xanthenes were obtained selectively as the exclusive product.…”

Section: Des In Organocatalysis: Reactive Basic or Acidic Solvents Fomentioning

confidence: 99%

“…In these cases, the reaction consisted of a high loading of a mixture of an aldehyde (0.53 kg L −1 ) and dimedone (0.14 kg L −1 ) in DES heated at 80 °C under stirring for 2–6 h. With 1:2 ChCl/urea (molar ratio) DES, tetraketones were obtained selectively as the only product, whereas for the 1:2 ChCl/ZnCl 2 (molar ratio) DES, xanthenes were obtained selectively as the exclusive product. This is the first example of the use of DES control in xanthenes and tetraketones synthesis by changing the DES component (Table ) …”

Section: Des In Organocatalysis: Reactive Basic or Acidic Solvents Fomentioning

confidence: 99%

Deep Eutectic Solvents for Organocatalysis, Biotransformations, and Multistep Organocatalyst/Enzyme Combinations

et al. 2015

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Deep eutectic solvents (DES) have emerged as promising solutions in many areas of chemistry. DES have many of the advantages of ionic liquids (e.g., low vapor pressure, nonflammability, tunability, etc.) but have lower costs, straightforward syntheses, and are often biodegradable. In this minireview, we discuss briefly the applications of DES in areas such as biotransformations, organocatalysis, and combinations of these that lead to multistep processes. DES can be used as solvents, cosolvents, performance additives for bio‐ and organocatalysis, tools to anchor organocatalysts selectively, or for extraction/separation. Several DES have been used both as solvents and organocatalysts at the same time. Given their promising features, it may be expected that many applications in these areas will appear in the coming years.

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“…1A) results from the reaction between salicylaldehydes with two equivalents of cyclic-1,3-diones [14][15][16][17][18][19][20], while tetraketones ( Fig. 1B) result from the reaction between the same diketones with aromatic aldehydes, devoid of the ortho-hydroxyl group [21][22][23][24]. Among these, 1-oxo-hexahydroxanthenes are known for their important pharmacological properties, such as anti-estrogenic, antimicrobial, hypoglycaemic, antibacterial and thrombin inhibitory activities and serve as neuropeptide YY5 receptor antagonists [25][26][27][28], while tetraketones are known to possess antitumor activity [29][30][31][32].…”

Section: Introductionmentioning

confidence: 98%

Sulfamic acid-catalyzed, environmentally benign synthesis of bis-tetronic acids at ambient temperature

et al. 2016

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An enviro-economic protocol has been described for the synthesis of bistetronic acids by pseudo-three-component condensation between aldehydes/isatins and tetronic acid using sulfamic acid as a solid acid catalyst. Easy commercial availability of the catalyst at extremely low cost, excellent yields and avoidance of conventional purification procedures are the main merits of this energy efficient protocol. Graphical AbstractO O O Sulfamic acid EtOH, RT

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Chemoselective synthesis of xanthenes and tetraketones in a choline chloride-based deep eutectic solvent

Cited by 56 publications

References 35 publications

Deep Eutectic Solvents: The Organic Reaction Medium of the Century

Deep Eutectic Solvents: The Organic Reaction Medium of the Century

Deep Eutectic Solvents for Organocatalysis, Biotransformations, and Multistep Organocatalyst/Enzyme Combinations

Sulfamic acid-catalyzed, environmentally benign synthesis of bis-tetronic acids at ambient temperature

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