Coumarin synthesis via Pechmann condensation: toward a greener era (microreview)

Gonçalves, Guilherme Arraché; Eifler‐Lima, Vera Lucia

doi:10.1007/s10593-021-02975-7

Cited by 5 publications

(7 citation statements)

References 15 publications

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“…Schematic outline 1C illustrates the synthesis of the NIR-responsive cross-linker. Initially, Cou-Cl, a coumarin derivative, was obtained by the Pechman condensation and transformed into Cou–OH via hydrolysis with copper(II) sulfate pentahydrate . The yields of these two reactions were 90 and 89%, respectively.…”

Section: Resultsmentioning

confidence: 99%

“…34 These modifications include the addition of thiols, 35 methacrylates, 36 and alkyne/azide functionalities for cancer therapy. 37 However, by functionalizing alginate with norbornene, it could undergo a copper-free IEDDA click reaction, which was useful for the formation of injectable hydrogels. 9 A carbodiimide coupling reaction was performed to functionalize Alg with Nb-NH 2 .…”

Section: ■ Materials and Methodsmentioning

confidence: 99%

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Injectable and Multifunctional Hydrogels Based on Poly(N-acryloyl glycinamide) and Alginate Derivatives for Antitumor Drug Delivery

Vu,

Jo,

Kim

et al. 2024

ACS Appl. Mater. Interfaces

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Chemotherapy is a conventional treatment that uses drugs to kill cancer cells; however, it may induce side effects and may be incompletely effective, leading to the risk of tumor recurrence. To address this issue, we developed novel injectable thermal/near-infrared (NIR)-responsive hydrogels to control drug release. The injectable hydrogel formulation was composed of biocompatible alginates, poly(N-acryloyl glycinamide) (PNAGA) copolymers with an upper critical solution temperature, and NIR-responsive cross-linkers containing coumarin groups, which were gelated through bioorthogonal inverse electron demand Diels−Alder reactions. The hydrogels exhibited quick gelation times (120−800 s) and high drug loading efficiencies (>90%). The hydrogels demonstrated a higher percentage of drug release at 37 °C than that at 25 °C due to the enhanced swelling behavior of temperature-responsive PNAGA moieties. Upon NIR irradiation, the hydrogels released most of the entrapped doxorubicin (DOX) (97%) owing to the cleavage of NIR-sensitive coumarin ester groups. The hydrogels displayed biocompatibility with normal cells, while induced antitumor activity toward cancer cells. DOX/hydrogels treated with NIR light inhibited tumor growth in nude mice bearing tumors. In addition, the injected hydrogels emitted red fluorescence upon excitation at a green wavelength, so that the drug delivery and hydrogel degradation in vivo could be tracked in the xenograft model.

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Section: Resultsmentioning

confidence: 99%

Section: ■ Materials and Methodsmentioning

confidence: 99%

Injectable and Multifunctional Hydrogels Based on Poly(N-acryloyl glycinamide) and Alginate Derivatives for Antitumor Drug Delivery

Vu,

Jo,

Kim

et al. 2024

ACS Appl. Mater. Interfaces

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“…Decarboxylation of phenolic acids ( R 61 and R 64) yielded hydroxyphenols, e.g., resorcinol and catechol. Resorcinol may further react with formyl acetate via the Pechmann condensation ( R 65) producing 3-acetyl-4-hydroxy-2 H -chromen-2-one . Since the acetyl group was highly reactive with the amine group of 2-aminophenol (i.e., the amination product of catechol, R 63), their interaction led to precipitating ( Z )-3-(1-((4-hydroxyphenyl)amino)ethylidene)-chromane-2,4-dione in the hydrochar ( R 66), as shown in Figure .…”

Section: Resultsmentioning

confidence: 99%

Reactivity and Stability of Natural Clay Minerals with Various Phyllosilicate Structures as Catalysts for Hydrothermal Liquefaction of Wet Biomass Waste

Sudibyo

Cabrera

Widyaparaga

et al. 2023

Ind. Eng. Chem. Res.

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We evaluated natural clay minerals representing all classes of phyllosilicates as in situ catalysts for hydrothermal liquefaction (HTL) of anaerobically digested cattle manure at 350 °C for 1 h, i.e., kaolinite, montmorillonite, talc, vermiculite, phlogopite, meixnerite, attapulgite, and alumina. The relative compositions of strong Bronsted (SBrA), strong Lewis (SLA), and weak Lewis acidic (WLA) sites and the strong (SBS) and weak (WBS) basic sites of clay minerals significantly affected the formation of HTL products (i.e., biocrude oil, hydrochar, and aqueous-and gas-phase coproducts) and the distribution and speciation of elements. The general mechanistic roles of these active sites are as follows: (1) SBrA catalyzed the biocrude-forming reactions and inhibited the hydrochar-repolymerizing reactions; (2) SLA promoted the production of hydrochar precursors; (3) WLA enhanced the hydrodeoxygenation, hydrodenitrogenation, and hydrodesulfurization of biocrude by utilizing the hydrogen generation catalyzed by WBS; and (4) SBS increased the production of organic acids solubilizing nutrients into the aqueous-phase coproduct (HTL-AP). Montmorillonite was the most suitable for the HTL catalyst due to the optimal composition of these active sites, leading to achieving maximal biocrude energy recovery (i.e., 82%) with low heteroatoms content (i.e., 15% O, 0.24% N, and 0.08% S), minimal hydrochar yield (i.e., 10%), and maximal nutrient yield in HTL-AP, i.e., 71% P, 54% Mg, 29% NH 3 -N, and 14% Ca. In addition, the crystalline structure of montmorillonite remained intact after the HTL process. This study informs comprehensive catalytic roles of different surface-active sites of clay minerals useful for future development of clay-based catalysts for more sustainable overall HTL systems.

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“…The first pathway was the Pechmann condensation of resorcinol with formyl acetate (L18) producing 4-hydroxy-2 H -chromen-2-one in the biocrude. 75 Acetylation of this compound (L19) into 3-acetyl-4-hydroxy-2 H -chromen-2-one 76 allowed the formation of ( Z )-3-(1-((4-hydroxyphenyl)amino)ethylidene)chromane-2,4-dione in the hydrochar because the acetyl group was susceptible to condensation (L20) with the amine group of 2-aminophenol, i.e. , the amination product of catechol.…”

Section: Resultsmentioning

confidence: 99%

“…The rst pathway was the Pechmann condensation of resorcinol with formyl acetate (L18) producing 4-hydroxy-2H-chromen-2-one in the biocrude. 75 Acetylation of this compound (L19) into 3-acetyl-4-hydroxy-2H-chromen-2-one 76 allowed the formation of (Z)-3-(1-((4-hydroxyphenyl)amino)ethylidene)chromane-2,4-dione in the hydrochar because the acetyl group was susceptible to condensation (L20) with the amine group of 2-aminophenol, i.e., the amination product of catechol. 77 The second pathway was regioselective nucleophilic addition involving a nitrogen atom of benzoic acid-derived phenylhydrazine with carbonyl carbon of ethylacetoacetate, 78 followed by intramolecular cyclization with the ester group of ethylacetoacetate and the other nitrogen atom of phenylhydrazine to produce phenylpyrazolone (C42).…”

Section: Mechanistic Interpretationmentioning

confidence: 99%

Probing elemental speciation in hydrochar produced from hydrothermal liquefaction of anaerobic digestates using quantitative X-ray diffraction

Sudibyo

Tester

2022

Sustainable Energy Fuels

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Coumarin synthesis via Pechmann condensation: toward a greener era (microreview)

Cited by 5 publications

References 15 publications

Injectable and Multifunctional Hydrogels Based on Poly(N-acryloyl glycinamide) and Alginate Derivatives for Antitumor Drug Delivery

Injectable and Multifunctional Hydrogels Based on Poly(N-acryloyl glycinamide) and Alginate Derivatives for Antitumor Drug Delivery

Reactivity and Stability of Natural Clay Minerals with Various Phyllosilicate Structures as Catalysts for Hydrothermal Liquefaction of Wet Biomass Waste

Probing elemental speciation in hydrochar produced from hydrothermal liquefaction of anaerobic digestates using quantitative X-ray diffraction

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