An efficient synthesis of tetrahydropyrazolopyridine derivatives by a one-pot tandem multi-component reaction in a green media

MaGee, David I.; Dabiri, Minoo; Salehi, Peyman; Koohshari, Majid; Hajizadeh, Zoleikha

doi:10.3998/ark.5550190.p008.462

Cited by 7 publications

(2 citation statements)

References 12 publications

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“…Despite its incredible advantages, XG has several limitations, such as low specific surface area, heat resistance, difficulty in processability, insolubility in common organic solvents, instability and relatively poor hydrodynamic volume 33 . The chemical functionalization of this natural polymer by magnetic nanomaterials, supramolecules, synthetic polymers and also network formation of the natural polymers can be effectively enhancing their structural and chemical properties making them a promising candidate for organic reaction 34 , 35 .…”

Section: Introductionmentioning

confidence: 99%

Utilizing magnetic xanthan gum nanocatalyst for the synthesis of acridindion derivatives via functionalized macrocycle Thiacalix[4]arene

Hassanzadeh-Afruzi,

Salehi,

Ranjbar

et al. 2023

Sci Rep

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An effective method for synthesizing acridinedione derivatives using a xanthan gum (XG), Thiacalix[4]arene (TC4A), and iron oxide nanoparticles (IONP) have been employed to construct a stable composition, which is named Thiacalix[4]arene-Xanthan Gum@ Iron Oxide Nanoparticles (TC4A-XG@IONP). The process used to fabricate this nanocatalyst includes the in-situ magnetization of XG, its amine modification by APTES to get NH2-XG@IONP hydrogel, the synthesis of TC4A, its functionalization with epichlorohydrine, and eventually its covalent attachment onto the NH2-XG@IONP hydrogel. The structure of the TC4A-XG@IONP was characterized by different analytical methods including Fourier-transform infrared spectroscopy, X-Ray diffraction analysis (XRD), Energy Dispersive X-Ray, Thermal Gravimetry analysis, Brunauer–Emmett–Teller, Field Emission Scanning Electron Microscope and Vibration Sample Magnetomete. With magnetic saturation of 9.10 emu g−1 and ~ 73% char yields, the TC4As-XG@IONP catalytic system demonstrated superparamagnetic property and high thermal stability. The magnetic properties of the TC4A-XG@IONP nanocatalyst system imparted by IONP enable it to be conveniently isolated from the reaction mixture by using an external magnet. In the XRD pattern of the TC4As-XG@IONP nanocatalyst, characteristic peaks were observed. This nanocatalyst is used as an eco-friendly, heterogeneous, and green magnetic catalyst in the synthesis of acridinedione derivatives through the one-pot pseudo-four component reaction of dimedone, various aromatic aldehydes, and ammonium acetate or aniline/substituted aniline. A combination of 10 mg of catalyst (TC4A-XG@IONP), 2 mmol of dimedone, and 1 mmol of aldehyde at 80 °C in a ethanol at 25 mL round bottom flask, the greatest output of acridinedione was 92% in 20 min.This can be attributed to using TC4A-XG@IONP catalyst with several merits as follows: high porosity (pore volume 0.038 cm3 g−1 and Pore size 9.309 nm), large surface area (17.306 m2 g−1), three dimensional structures, and many catalytic sites to active the reactants. Additionally, the presented catalyst could be reused at least four times (92–71%) with little activity loss, suggesting its excellent stability in this multicomponent reaction. Nanocatalysts based on natural biopolymers in combination with magnetic nanoparticles and macrocycles may open up new horizons for researchers in the field.

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Section: Introductionmentioning

confidence: 99%

Utilizing magnetic xanthan gum nanocatalyst for the synthesis of acridindion derivatives via functionalized macrocycle Thiacalix[4]arene

Hassanzadeh-Afruzi,

Salehi,

Ranjbar

et al. 2023

Sci Rep

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“…15 THDPPs are also the fused heterocycle products of a modified pseudo-six-component reaction of hydrazine and 1,3-dicarbonyl compounds with aldehydes and ammonium acetate, and they are formed via a pyrazolone intermediate produced in situ. [15][16][17][18][19][20] In addition to the use of various catalysts and organic solvents for the synthesis of THDPPs, an ultrasound-assisted version of an MCR has also recently been documented. 15b However, there is still a need for cleaner and more-efficient ecofriendly routes for largescale synthesis of THDPPS in water.…”

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confidence: 99%

Advanced Catalyst-Free Pseudo-Six-Component Synthesis of Tetrahydrodipyrazolopyridines in Water by Using Ammonium Carbonate as an Ecofriendly Source of Nitrogen

Tamaddon

Khorram²

2020

Synlett

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This work describes an improved environmentally friendly method for the synthesis of tetrahydrodipyrazolopyridines (THDPPs) in water through a catalyst-free pseudo-six-component reaction of alkyl acetoacetates, hydrazine hydrate, and ammonium carbonate with an aldehyde in a mole ratio of 2:2:1:1 at room temperature. The ammonium carbonate serves as a green source of nitrogen for the central 1,4-dihydropyridine ring in the THDPPs. Methyl acetoacetate reacts faster than either ethyl or propyl acetoacetate in this method. The product precipitates during the reaction and is simply collected by filtration. Advantages of this environmentally benign method include no use of an organic solvent, no hazardous waste, rapid clean reactions, and excellent yields of products.

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An Efficient and Eco‐Friendly One‐Pot Synthesis of Pyrazolopyridines Mediated by Choline Chloride/Urea Eutectic Mixture

2019

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In this contribution several choline chloride-based deep eutectic solvents were evaluated as novel reaction media for the multicomponent one-pot synthesis of pyrazolopyridine derivatives. It was found that the reaction between hydrazines, ethyl acetoacetate, ammonium acetate and aldehydes or ketones is efficiently catalyzed by the eutectic mixture choline chloride/urea yielding a wide variety of tetrahydrodipyrazolopyridine derivatives in good to excellent yields. In addition, the low melting mixture was reused in four cycles without observing a detrimental catalytic activity.

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An efficient synthesis of tetrahydropyrazolopyridine derivatives by a one-pot tandem multi-component reaction in a green media

Abstract: The synthesis of some tetrahydropyrazolopyridine derivatives has been described by a one-pot 2A + 2B + C + D four component reaction of a 1,3-dicarbonyl compound, an aldehyde, hydrazine and ammonium acetate in ethanol as a green media under catalyst-free condition.

Cited by 7 publications

References 12 publications

Utilizing magnetic xanthan gum nanocatalyst for the synthesis of acridindion derivatives via functionalized macrocycle Thiacalix[4]arene

Utilizing magnetic xanthan gum nanocatalyst for the synthesis of acridindion derivatives via functionalized macrocycle Thiacalix[4]arene

Advanced Catalyst-Free Pseudo-Six-Component Synthesis of Tetrahydrodipyrazolopyridines in Water by Using Ammonium Carbonate as an Ecofriendly Source of Nitrogen

An Efficient and Eco‐Friendly One‐Pot Synthesis of Pyrazolopyridines Mediated by Choline Chloride/Urea Eutectic Mixture

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