Synthesis of Pyrazolo[3,4‐<i>d</i>]pyrimidin‐4‐ones Catalyzed by Br?nsted‐acidic Ionic Liquids as Highly Efficient and Reusable Catalysts

Tavakoli‐Hoseini, Niloofar; Moloudi, Raheleh; Davoodnia, Abolghasem; Shaker, Mohammad

doi:10.1002/cjoc.201180411

Cited by 23 publications

(6 citation statements)

References 45 publications

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“…These reactions offer several advantages in preparative procedures such as environmental compatibility, simplification of work-ups, formation of cleaner products, enhanced selectivity, reduction of by-products, a reduction in waste produced, and much improved reaction rates. Therefore, we decided to investigate the efficiency of [Et 3 Table 2). As can be seen, the efficiency of the reaction is affected mainly by the amount of the catalyst and the reaction temperature.…”

Section: Catalytic Performance Of [Et 3 Nc 4 So 3 H][hso 4 ]/Al 2 O 3mentioning

confidence: 99%

“…[1][2][3][4] The introduction of structural functionalities on the cationic or anionic part has made it possible to design new ILs with specific properties. [5] SO 3 H-functionalized ILs can be used as highly efficient acid catalysts and have been receiving extensive interest as green substitute for H 2 SO 4 , HF, and AlCl 3 catalysts in chemical processes.…”

Section: Introductionmentioning

confidence: 99%

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Alumina Supported Acidic Ionic Liquid: Preparation, Characterization, and Its Application as Catalyst in the Synthesis of 1,8-dioxo-octahydroxanthenes

Khoshnevis

Davoodnia

Zare-Bidaki

et al. 2013

Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-

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Preparation of a novel heterogeneous acidic catalyst by impregnation of alumina support by N-(4-sulfonic acid)butyl triethylammonium hydrogen sulfate ([Et 3 NC 4 SO 3 H][HSO 4 ]), an acidic ionic liquid, and its primary application as a solid acidic supported catalyst in the synthesis of 1,8-dioxo-octahydroxanthenes by reaction of dimedone with aromatic aldehydes are described. Characterization of the catalyst was performed by FT-IR, BET, TG/DTG, and XRD techniques. The results showed that the catalyst has high activity and the desired products were obtained in high yields. Moreover, the recovered catalyst was found to be reusable and a considerable catalytic activity still could be achieved after third run.

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Section: Catalytic Performance Of [Et 3 Nc 4 So 3 H][hso 4 ]/Al 2 O 3mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Alumina Supported Acidic Ionic Liquid: Preparation, Characterization, and Its Application as Catalyst in the Synthesis of 1,8-dioxo-octahydroxanthenes

Khoshnevis

Davoodnia

Zare-Bidaki

et al. 2013

Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-

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“…The most attractive highlight of this reaction was very short reaction time, simple isolation of product, high yield, use of non-hazardous organic solvents, and recyclable and reusable capacity of catalysts (Scheme 66). [95] Mechanism: The plausible mechanism for preparation for pyrazolo [3,4-d]pyrimidin-4-ones suggests that the formation of reaction intermediate is facilitated by ionic liquid (Figure 18).…”

Section: Synthesis Of Pyrazolopyrimidine Using Acidic/ Basic/neutral Ionic Liquid As Reaction Mediummentioning

confidence: 99%

Efficient Green Protocols for the Preparation of Pyrazolopyrimidines

et al. 2021

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Pyrazolopyrimidine with all its isoforms occupy a noteworthy position in medicinal chemistry owing to their proven dominance in the modulation of a vast array of biological receptors, thereby mitigating numerous pathological conditions. The development of sustainable protocols, which integrate the principles of green chemistry in the synthesis process although challenging, offers the most appropriate way to conduct the sustainable synthesis of pyrazolopyrimidines. Due to the effectiveness of this nucleus and striking similarity to purines, they have been accessed using green as well as non-green protocols. Analytical techniques like 2D NMR has been employed for the confirmation of pyrazolopyrimidines and their isomers besides the conventional single-crystal X-ray diffraction (XRD). Here, considering the rising awareness of sustainable protocols, we aimed at exploring this decade for green protocols for the synthesis of pyrazolopyrimidines and furnished products in excellent yields in this review. Protocols covered in this review include synthesis using green solvent, solvent-free conditions, green catalyst, and catalyst-free reactions. Also, synthesis of pyrazolopyrimidines assisted by microwave and ultrasound, as well as ionic liquid mediated synthesis are covered. It is estimated that this review shall throw some light upon the environmentally benign protocols to produce pyrazolopyrimidines which is itself a very important nucleus in the field of medicinal chemistry.

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“…[15][16][17] This claim usually rests on the fact that ionic liquids are thermally stable, and recyclable under ambient conditions. [18][19][20] The development of ionic liquids for use as solvents offers advantages for a wide variety of chemical processes, which might be the best possible solvents to try a reaction in them due to their unique characters. [21][22][23][24][25] Heck reaction, one of the most important methodologies for C-C bond formation in general organic synthesis, was also studied in ionic liquids to investigate catalytic processes.…”

Section: Introductionmentioning

confidence: 99%

Investigation on the Coordination Mode of IL‐Supported Diols Used as Phosphine‐Free Ligands for Palladium Catalyzed Heck Reaction

2013

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The coordination mode of IL-supported diols used as phosphine-free ligands for palladium catalyzed Heck reaction has been investigated by tuning their compositions. The difference in coordination of these IL-supported diols with metal Pd in Heck reaction was related to the changes of the cation rings, leading to the different activities of Pd catalyst in the reaction. The experimental results indicated that the activities of Pd catalyst were affected mainly by π-electron density of the cation rings. Compared to pyridinium and piperidinium cations, imidazolium cations showed the best coordination to metal Pd. In the meantime, C-2 hydrogen and the length of alkyl side chains had impacts on the coordination as well.

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Synthesis of Pyrazolo[3,4‐d]pyrimidin‐4‐ones Catalyzed by Br?nsted‐acidic Ionic Liquids as Highly Efficient and Reusable Catalysts

Cited by 23 publications

References 45 publications

Alumina Supported Acidic Ionic Liquid: Preparation, Characterization, and Its Application as Catalyst in the Synthesis of 1,8-dioxo-octahydroxanthenes

Alumina Supported Acidic Ionic Liquid: Preparation, Characterization, and Its Application as Catalyst in the Synthesis of 1,8-dioxo-octahydroxanthenes

Efficient Green Protocols for the Preparation of Pyrazolopyrimidines

Investigation on the Coordination Mode of IL‐Supported Diols Used as Phosphine‐Free Ligands for Palladium Catalyzed Heck Reaction

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