Green catalytic synthesis of 14-aryl-14<i>H</i>-dibenzo[a,j]xanthenes using recyclable mesoporous zirconia modified with tungstophosphoric acid

Rivera, Toa S.; Blanco, Mirta N.; Pizzio, Luis R.; Romanelli, Gustavo Pablo

doi:10.1080/17518253.2012.665947

Cited by 9 publications

(4 citation statements)

References 39 publications

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“…On the other hand, the substituents at the 1,2-diketone had no significant effects on the yield to the corresponding products. Since only symmetric 1,2-diketones were used for the condensation reaction, no regioisomers were generated as the products (Table 1, entries [7][8][9][10][11].…”

Section: Synthesis Of Quinoxaline Derivativementioning

confidence: 99%

“…10 We recently reported a procedure for the 14-aryl-14H-dibenzo[a,j]xanthenes using recyclable mesoporous zirconia modified with tungstophosphoric acid. 11 On the other hand, quinoxaline derivatives are a very important class of nitrogencontaining heterocycles as they constitute useful intermediates in organic synthesis. 12 This structure plays an important role in the design of a number of heterocyclic compounds with different biological activities, making this type of compounds important in the field of medicine as antitumor, anticonvulsant, antimalarial, anti-inflammatory, antiamoebic, antioxidant, antidepressant, antiprotozoal, antibacterial, and anti-HIV agents.…”

Section: Introductionmentioning

confidence: 99%

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Tungstophosphoric Acid Supported on Zirconia: A Recyclable Catalyst for the Green Synthesis on Quinoxaline Derivatives under Solvent-Free Conditions

Sosa

Rivera

Blanco

et al. 2013

Phosphorus, Sulfur, and Silicon and the Related Elements

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A green, simple, and fast procedure has been developed for the preparation of quinoxaline derivatives by a condensation of 1,2-diamines with 1,2-dicarbonyl compounds in the presence of zirconium oxide modified with tungstophosphoric acid (H 3 PW 12 O 40 ) as a heterogeneous catalyst, in a solvent-free medium using conventional heating. Quinoxaline derivatives were formed in short-time periods and excellent yields (65-100%). The reaction work-up is very simple and the catalyst can be easily separated from the reaction mixture and reused several times in subsequent reactions without appreciable loss of the catalytic activity. Supplementary materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfer, and Silicon and the Related Elements for the following free supplemental files: Additional text.

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Section: Synthesis Of Quinoxaline Derivativementioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Tungstophosphoric Acid Supported on Zirconia: A Recyclable Catalyst for the Green Synthesis on Quinoxaline Derivatives under Solvent-Free Conditions

Sosa

Rivera

Blanco

et al. 2013

Phosphorus, Sulfur, and Silicon and the Related Elements

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“…The reaction was performed using dimedone (1 mmol), 3,4-methhylenedioxyphenol or 2-naphthol (1 mmol), and aldehyde (1 mmol) in the presence of 0.02 g of CD-NH 2 /PMo 12 in water (5 mL), at 100 • C for a time period of 1.5-3.2 h. In this condition seven compounds of xanthenes derived from 2-naphthol (87-92%) and nine compounds of 3,4-methhylene-dioxyphenol (88-95%) were obtained (Scheme 24). Similarly, Rivera et al [94,95] reported a green method to prepare xanthene derivatives from naphthol using tungstophosphoric acid/zirconia (Zr/PW 12 ) composites prepared by the sol-gel method. In total, 10 compounds of 14-aryl-14H-dibenzo[a,j]xanthenes were obtained with yields between 78 and 99, using aldehyde (1.2 mmol), 2-naphthol (2 mmol), and catalyst (0.01 mmol%), at a temperature of 130 • C in a reaction time between 1 and 5 h. Gharib [96].…”

Section: Chromenes and Xanthenesmentioning

confidence: 99%

Recent Applications of Heteropolyacids and Related Compounds in Heterocycle Synthesis. Contributions between 2010 and 2020

et al. 2021

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Over the past two decades, polyoxometalates (POM) have received considerable attention as solid catalysts, due to their unique physicochemical characteristics, since, first, they have very strong Bronsted acidity, approaching the region of a superacid, and second, they are efficient oxidizers that exhibit rapid redox transformations under fairly mild conditions. Their structural mobility is also highlighted, since they are complex molecules that can be modified by changing their structure or the elements that compose them to model their size, charge density, redox potentials, acidity, and solubility. Finally, they can be used in substoichiometric amounts and reused without an appreciable loss of catalytic activity, all of which postulate them as versatile, economic and ecological catalysts. Therefore, in 2009, we wrote a review article highlighting the great variety of organic reactions, mainly in the area of the synthesis of bioactive heterocycles in which they can be used, and this new review completes that article with the contributions made in the same area for the period 2010 to 2020. The synthesized heterocycles to be covered include pyrimidines, pyridines, pyrroles, indoles, chromenes, xanthenes, pyrans, azlactones, azoles, diazines, azepines, flavones, and formylchromones, among others.

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“…Among the heterogeneous catalysts, heteropolyacids (HPAs) and related compounds are a field of increasing importance worldwide. We reported the use of an HPA catalyst with a Keggin structure for different organic transformation reactions, for example, azlactones [10], quinoxalines [11], xanthenes [12], dihydropyrimidinones [13], hexahydropyrimidines [14], quinolines [15], and imidazoles [16].…”

Section: Introductionmentioning

confidence: 99%

Green and Efficient Synthesis of Flavones and Chromones Using Heteropolyacids as Catalyst in Glycerol

Migliorero

Palermo

Durango

et al. 2018

LOC

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Organic solvents are required to carry out most organic transformations, which cause environmental pollution because of their low volatility. Glycerol, a side product obtained from biodiesel production, has emerged as a friendly solvent due to its advantageous properties. In this paper, an efficient procedure for the synthesis of flavones and chromones, using heteropolyacids as recyclable catalyst and glycerol as the solvent, is presented. The use of heteropolyacids as catalysts allows for excellent yields, easy separation and recovery, low environmental impact, and low cost. Glycerol can also be readily recovered and used over again. In addition, the presented method provides other advantages such as the low formation of waste and the replacement of corrosive mineral acids.

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Green catalytic synthesis of 14-aryl-14H-dibenzo[a,j]xanthenes using recyclable mesoporous zirconia modified with tungstophosphoric acid

Cited by 9 publications

References 39 publications

Tungstophosphoric Acid Supported on Zirconia: A Recyclable Catalyst for the Green Synthesis on Quinoxaline Derivatives under Solvent-Free Conditions

Tungstophosphoric Acid Supported on Zirconia: A Recyclable Catalyst for the Green Synthesis on Quinoxaline Derivatives under Solvent-Free Conditions

Recent Applications of Heteropolyacids and Related Compounds in Heterocycle Synthesis. Contributions between 2010 and 2020

Green and Efficient Synthesis of Flavones and Chromones Using Heteropolyacids as Catalyst in Glycerol

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