Deep Eutectic Solvent Catalyzed One-Pot Synthesis of 4,7-Dihydro-1<i>H</i>-pyrazolo[3,4-<i>b</i>]pyridine-5-carbonitriles

高歌,; 王萍,; Peng, Liu; 张卫红,; 默丽萍,; 张占辉,

doi:10.6023/cjoc201711014

Cited by 46 publications

(16 citation statements)

References 14 publications

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“…Deep eutectic solvents (DESs) have known as a new generation of ionic liquid attracting much interest in the field of organic synthesis and sustainable chemistry [1, 2, 3, 4, 5, 6, 7, 8, 9]. DESs are non-volatile substances with some typical characteristic as nonflammability, thermal stability, simple preparation and purification, low cost, biodegradation.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of a new series of 2-hydroxy-5-iodo-N’-(1-arylethylidene)benzohydrazides using a deep eutectic solvent as solvent/catalyst under sonication

Nguyen

Tran

2019

Heliyon

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We report here the preparation of 2-hydroxy-5-iodo- N ’-(1-arylethylidene)benzohydrazide compounds in good to excellent yields (83–98%) within a short reaction time (10–15 min), through a clean and efficient procedure. Seventeen new compounds were synthesized and fully characterized by FT-IR, NMR, and HRMS. The deep eutectic solvent can be recovered easily by phase extraction and can be reused up to several times without any significant loss of catalytic activity. Additionally, the method has a wide substrate scope and provides an accessible route for the large-scale direct synthesis of 2-hydroxy-5-iodo- N ’-(1-arylethylidene)benzohydrazides.

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Section: Introductionmentioning

confidence: 99%

Synthesis of a new series of 2-hydroxy-5-iodo-N’-(1-arylethylidene)benzohydrazides using a deep eutectic solvent as solvent/catalyst under sonication

Nguyen

Tran

2019

Heliyon

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“…Interestingly, the synthesis of DESs can be carried out easily by mixing two or three cheap and available components [25] . The prominent features of DES are inexpensive, biodegradable so that DES can be applied for industrial processes [20,26–27] . DES has been studied and applied intensively in organic synthesis such as C−C, C−O, C−N, C−S bond formation [28–36] …”

Section: Introductionmentioning

confidence: 99%

Intermolecular and Intramolecular Friedel‐Crafts Acylation of Carboxylic Acids using Binary Ionic Liquids: An Experimental and Computational Study

Nguyen

Tran

et al. 2022

ChemistrySelect

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Traditional Friedel‐Crafts acylation with acid halides suffers from waste byproducts such as SO2, HCl, and the hydrolysis of Lewis acid catalyst. Thus, the environmentally benign intermolecular and intramolecular Friedel‐Crafts acylation of arenes with carboxylic acids as acylating agents has been investigated using a mixture of deep eutectic solvent and an ionic liquid as reaction media under microwave irradiation. The Friedel‐Crafts acylations with carboxylic acids as acylating agents are challenging due to the low reactivity of carboxylic acids. In this paper, the desired products were obtained at moderate to good yields under microwave irradiation for a short reaction time. The Friedel‐Crafts cyclization of 4‐phenylbutyric acid is more effective than 3‐phenylpropionoic acid under the present method. The reaction mechanism is proposed by combining experiments with density functional theory calculations, highlighting the critical role of ZnCl2, triflate anion (CF3COO−) in binary ionic liquids, and acidic conditions in accomodating a kinetic accessible pathway making the C−C bond.

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“…These purification procedures not only result in high manufacturing cost and environmental contamination but also prevent subsequent direct transformations. To resolve these issues, remarkable efforts have been devoted toward developing quantitative synthetic reaction routes and replacing organic solvents with green reaction mediums (water, − ionic liquids, − biomass solvent, , and so on , ). While significant progress has been made in the development of eco-friendly synthetic reactions in green reaction mediums, there are only a limited number of reactions with decent yields available, and the majority still suffer from mediocre reaction yields, which call for synthetic improvement on reaction conversion and selectivity.…”

Section: Introductionmentioning

confidence: 99%

Practical Approach for Clean Preparation of Z-β-Thiocyanate Alkenyl Esters

Lin

Shu

et al. 2019

ACS Sustainable Chem. Eng.

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A practical and eco-friendly method for the clean preparation of a variety of Z-β-thiocyanate alkenyl esters via lactic acid-catalyzed multicomponent hydrothiocyanation reaction was established. In the subgram-scale synthesis, Z-β-thiocyanate alkenyl esters were exclusively generated, and the product could be easily isolated in high purity via extraction. In the large-scale synthesis, the pure products could be simply collected through liquid–liquid separation. The eco-friendly lactic acid played a dual function in the transformation, serving as recyclable biomass catalyst and recyclable reaction medium.

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Deep Eutectic Solvent Catalyzed One-Pot Synthesis of 4,7-Dihydro-1H-pyrazolo[3,4-b]pyridine-5-carbonitriles

Cited by 46 publications

References 14 publications

Synthesis of a new series of 2-hydroxy-5-iodo-N’-(1-arylethylidene)benzohydrazides using a deep eutectic solvent as solvent/catalyst under sonication

Synthesis of a new series of 2-hydroxy-5-iodo-N’-(1-arylethylidene)benzohydrazides using a deep eutectic solvent as solvent/catalyst under sonication

Intermolecular and Intramolecular Friedel‐Crafts Acylation of Carboxylic Acids using Binary Ionic Liquids: An Experimental and Computational Study

Practical Approach for Clean Preparation of Z-β-Thiocyanate Alkenyl Esters

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