Alginate–copper microspheres as efficient and reusable heterogeneous catalysts for the one-pot synthesis of 4-organylselanyl-1<i>H</i>-pyrazoles

Souza, Jaqueline F. de; Aquino, Thalita F.B. de; Nascimento, José Edmilson R.; Jacob, Raquel G.; Fajardo, André R.

doi:10.1039/d0cy00778a

Cited by 22 publications

(6 citation statements)

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“…An intrinsic and pivotal characteristic of heterogeneous catalysts and support materials is their stability under harsh reaction conditions and different solvents. [ 43 ] To evaluate the stability of the PEI@PAA and PEI@PAAc/Cu 2+ microparticles, experiments were performed by keeping them under different solvents at high temperatures. The results concerning the weight variation of the microparticles are listed in Table 1.…”

Section: Resultsmentioning

confidence: 99%

Copper supported on polyethyleneimine‐coated microparticles for the efficient synthesis of organoselenium compounds

Souza

Aquino

Nunes

et al. 2022

Applied Organom Chemis

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Copper‐catalyzed reactions are in continuous evidence due to their attractive features, and the use of solid materials to support this metal has broadened the possibilities in terms of application. To demonstrate this, polyacrylic acid (PAAc) microparticles coated with polyethyleneimine (PEI) were synthesized and utilized to support Cu2+ ions. These hybrid microparticles were tested as heterogeneous catalysts in the synthesis of 3‐arylselanylindoles. Overall, products were synthesized in good to moderate yields using 10 mg of the catalyst containing a meager amount of Cu2+ (2 μmol). Also, the heterogeneous reaction mediated by PEI@PAAc/Cu2+ microparticles was more efficient than the homogeneous catalysis. Reuse experiments demonstrated that PEI@PAAc/Cu2+ microparticles show appreciable catalytic performance up to three consecutive runs under the tested experimental conditions. Overall, the PEI@PAAc/Cu2+ microparticles serve as a support material for Cu2+ and can be exploited as heterogeneous catalysts for the synthesis of organoselenium compounds.

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Section: Resultsmentioning

confidence: 99%

Copper supported on polyethyleneimine‐coated microparticles for the efficient synthesis of organoselenium compounds

Souza

Aquino

Nunes

et al. 2022

Applied Organom Chemis

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“…In the work of Souza et al [24], Alg-Cu +2 microspheres were prepared via an ion exchange process, and it was examined as a catalyst for the synthesis of some substituted pyrazoles. The resulted product was in excellent yield, and the catalyst activity still good even after five reactions.…”

Section: Applications Of Alginate Metal Complexes 41 Organic Synthesis Fieldmentioning

confidence: 99%

Alginate Metal Complexes and Their Application

Alkhayer¹

2022

Properties and Applications of Alginates

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Alginate is a natural polymer that can form complexes in the presence of multivalent metal. In this chapter, we summarized the newest alginate metal complexes application in many fields; organic synthesis, environmental and medical application. The main idea was about alginate complexes’ role in the drug delivery system as a chiral excipient to reach the enantioselective release in the case of chiral drugs. We also present a case study about the ketoprofen enantioselective release investigation from alginate mixed beads with two ion metal types.

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“…16 Recently, Fajardo and his group have reported a threecomponent reaction for the synthesis of selenoethers of pyrazoles using Cu 2+ immobilized on alginate-based microspheres (Alg−Cu 2+ ) (Scheme 1, eq d). 17 Cheng's research group reported selenylation of uracils in the presence of sodium iodide and H 2 O 2 in dimethyl sulfoxide (DMSO) medium from the reaction of uracil and diselenides (Scheme 1, eq e). 18 Wang et al reported an electrochemical method for the selenylation of uracils in the presence of NH 4 I (Scheme 1, eq f).…”

Section: ■ Introductionmentioning

confidence: 99%

“…Pires et al developed a three-component reaction of benzoylacetonitriles, arylhydrazines, and diaryl diselenides in the presence of molecular iodine as a catalyst (Scheme , eq c) . Recently, Fajardo and his group have reported a three-component reaction for the synthesis of selenoethers of pyrazoles using Cu 2+ immobilized on alginate-based microspheres (Alg–Cu 2+ ) (Scheme , eq d) . Cheng’s research group reported selenylation of uracils in the presence of sodium iodide and H 2 O 2 in dimethyl sulfoxide (DMSO) medium from the reaction of uracil and diselenides (Scheme , eq e) .…”

Section: Introductionmentioning

confidence: 99%

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Visible Light-Mediated C(sp²)–H Selenylation of Amino Pyrazole and Amino Uracils in the Presence of Rose Bengal as an Organophotocatalyst

2022

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Herein, we report an efficient methodology for the synthesis of alkyl, benzyl, and phenyl selenoethers of aminopyrazoles and aminouracils by C(sp2)–H functionalization in the presence of visible light and Rose Bengal as an organophotocatalyst. The reaction of amino pyrazole/iosothiazole/isoxazole or amino uracils with 0.5 equivalent of diphenyl/dibenzyl/diethyl diselenides in the presence of visible light in acetonitrile medium and a catalytic amount of Rose Bengal provided the corresponding phenyl, benzyl, or ethyl selenoethers in good to very good yields. We have also utilized some of the selenylated aminopyrazoles for the preparation of pyrazole-fused dihydropyrimidines tethered with arylselenoethers by a catalyst-free one-pot three-component reaction. The notable features of this methodology are metal-free reaction conditions, good to very good yields, use of an organic photocatalyst, and wide substrate scope; it is also applicable to gram-scale synthesis and provides selenoethers of medicinally important heterocycles such amio-pyrazole, isoxazole, isothiazole, and uracils.

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Alginate–copper microspheres as efficient and reusable heterogeneous catalysts for the one-pot synthesis of 4-organylselanyl-1H-pyrazoles

Abstract: This study demonstrates the facile preparation and use of alginate–Cu2+ microspheres in the catalysis of a new class of organoselenium substituted pyrazoles through one-pot reactions.

Cited by 22 publications

References 43 publications

Copper supported on polyethyleneimine‐coated microparticles for the efficient synthesis of organoselenium compounds

Copper supported on polyethyleneimine‐coated microparticles for the efficient synthesis of organoselenium compounds

Alginate Metal Complexes and Their Application

Visible Light-Mediated C(sp²)–H Selenylation of Amino Pyrazole and Amino Uracils in the Presence of Rose Bengal as an Organophotocatalyst

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Alginate–copper microspheres as efficient and reusable heterogeneous catalysts for the one-pot synthesis of 4-organylselanyl-1H-pyrazoles

Abstract: This study demonstrates the facile preparation and use of alginate–Cu2+ microspheres in the catalysis of a new class of organoselenium substituted pyrazoles through one-pot reactions.

Cited by 22 publications

References 43 publications

Copper supported on polyethyleneimine‐coated microparticles for the efficient synthesis of organoselenium compounds

Copper supported on polyethyleneimine‐coated microparticles for the efficient synthesis of organoselenium compounds

Alginate Metal Complexes and Their Application

Visible Light-Mediated C(sp2)–H Selenylation of Amino Pyrazole and Amino Uracils in the Presence of Rose Bengal as an Organophotocatalyst

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Visible Light-Mediated C(sp²)–H Selenylation of Amino Pyrazole and Amino Uracils in the Presence of Rose Bengal as an Organophotocatalyst