Ionic Liquid Containing Copper(I): A New, Green, Homogeneous, and Reusable Catalyst for Click Cyclization

Ahmady, Amanollah Zarei; Heidarizadeh, Fariba; Keshavarz, Mosadegh

doi:10.1080/00397911.2012.687424

Cited by 36 publications

(11 citation statements)

References 25 publications

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“…Keshavarz and his group reported the cycloaddition of α ‐azidoketones 1 and terminal alkynes to form 1, 4‐disubstituted‐1 H ‐1,2,3‐triazoles 175 using a reusable ionic liquid containing copper(I) catalyst (Scheme 35a) [68] . A similar azide‐alkyne cycloaddition using porous titania nanosphere supported gold nanoparticles as a catalyst under aqueous medium was reported by Muthusubramanian and co‐workers [69] .…”

Section: Five Membered N‐heterocycles From α‐Azidoketones/estersmentioning

confidence: 62%

Recent Advances onα‐Azidoketones and Esters in the Synthesis ofN‐Heterocycles

Maurya

Borkotoky

2022

Asian J Org Chem

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Organic azides have been proven to possess versatile reactivity that is utilized to synthesize a large number of molecular scaffolds. Among the azides, α‐azidoketones and esters have been widely explored to synthesize numerous high valued N‐heterocycles. The enhanced acidity of the methylene hydrogen atoms by adjacent carbonyl or ester groups of α‐azidoketones and esters largely attributes to their unique chemical behaviour. It has been mostly utilized in two ways: a) the azides have been directly treated with other reagents in a basic medium and b) they are converted into α‐azidovinylketones and esters through Knoevenagel condensation with aldehydes and subsequently treated with various reagents to access nitrogen heterocycles. This review provides a general outlook and concise report on α‐azidoketones and esters towards the synthesis of various N‐heterocycles such as pyrroles, indoles, pyrazoles, imidazoles, triazoles, pyridines, pyrimidine, pyrazine and many others.

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Section: Five Membered N‐heterocycles From α‐Azidoketones/estersmentioning

confidence: 62%

Recent Advances onα‐Azidoketones and Esters in the Synthesis ofN‐Heterocycles

Maurya

Borkotoky

2022

Asian J Org Chem

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“…As far as we know, there is no report on the use of 1,2,3-triazole rings as a cationic source of chemically non-inert, especially SO 3 H-functionalized 1,2,3-triazolium ionic hybrids. Consequently, in continuation to our previous research works on the synthesis of new 1,4-disubstituted-triazoles by click methodology [25][26][27],…”

Section: Introductionmentioning

confidence: 58%

“…In order to introduce novel organic-inorganic Brønsted acidic ionic solid (BAIS) catalysts for the preparation of spirooxindole derivatives, 1-benzyl-4-phenyl-1H-1,2,3-triazole and 1-benzyl-1H-1,2,3-triazole substrates were prepared at the first step according to the previous literature with some extra modifications (Scheme 1) [25][26][27]32]. Multicomponent click reaction of benzyl chloride, phenyl acetylene, and sodium azide in the presence of a catalytic amount of CuI in a mixture of PEG 400 -H 2 O at room temperature after 25 min furnished 1-benzyl-4-phenyl-1H-1,2,3-triazole in 92% yield (Scheme 1a).…”

Section: Resultsmentioning

confidence: 99%

Click approach to the novel 1,2,3-triazolium phosphotungstate organic–inorganic hybrids for the highly promoted synthesis of spirooxindoles

2021

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The synthesis and catalytic activity of three 1,2,3-triazole-based ionic organicinorganic hybrids as novel water-soluble catalysts for the efficient preparation of spirooxindole derivatives are described. At first, three different 1,2,3-triazoles were prepared by click reaction. Then, these synthesized compounds were reacted with 1,4-butane sultone to generate novel solid 1,2,3-triazolium-N-butyl sulfonate zwitterions. In the next step, the newly synthesized organic zwitterions were treated with an aqueous solution of phosphotungstic acid to give three novel 1,2,3-triazolium-N-butyl sulfonic acid phosphotungstates as targeted organic-inorganic hybrid catalysts. The prepared catalysts were fully characterized using FTIR, 1 H and 13 C NMR, XRD, elemental analysis (CHNS), ESI-MS, DSC, and TG techniques. The introduced novel SO 3 H-functionalized ionic hybrid catalysts have a cationic organic triazolium with phosphotungstate anion and are water-soluble with appropriate thermal stability. Their catalytic activity was explored for the synthesis of spirooxindoles via the three-component reaction of 1,3-dicarbonyl compounds, barbituric acid, and isatin derivatives. The synthesis of desired spirooxindole products was performed in acceptable times with excellent yields in the presence of low loading amount of the prepared 1,2,3-triazolium-N-butyl sulfonic acid phosphotungstate catalysts (10 mmol%) in water. Some highlighted superiorities of the introduced organic-inorganic hybrids in comparison with most of the previously reported catalysts are as follows: clean and straightforward preparation, novelty of the catalysts, green conditions, ease of recovery, and reusability up to three repeated runs with no significant decrease in the catalytic stability.

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“…(°C) Refs. 1 H H 5a 93 166–167 [ 58 ] 2 OMe H 5b 89 190–191 [ 58 ] 3 H Br 5c 86 145–146 [ 59 ] 4 H NO 2 5d 77 180–181 [ 60 ] 5 H Cl 5e 89 150–152 [ 59 ] 6 H OMe 5f 88 142–143 [ 59 ] 7 CF 3 H 5g 81 221–223 [ 58 ] 8 Me H 5h 85 165–167 [ 58 ] Phenacyl bromides (1 mmol), arylacetylene (1.2 mmol), K 2 CO 3 ...…”

Section: Resultsmentioning

confidence: 99%

Peanut shell as a green biomolecule support for anchoring Cu2O: a biocatalyst for green synthesis of 1,2,3-triazoles under ultrasonic irradiation

et al. 2019

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Cu 2 O supported on peanut shell (Cu 2 O@PS) was prepared by the reaction of copper acetate and peanut shell powder as a naturally available biopolymer support. The prepared catalyst was used as an efficient and reusable heterogeneous catalyst in the click reaction of benzyl halide or phenacyl bromides, acetylenes and sodium azide for the synthesis of potentially biologically active 1,2,3-triazoles under ultrasonic irradiation in EtOH-H 2 O as green solvent. Electronic supplementary material The online version of this article (10.1186/s13065-019-0612-9) contains supplementary material, which is available to authorized users.

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Ionic Liquid Containing Copper(I): A New, Green, Homogeneous, and Reusable Catalyst for Click Cyclization

Cited by 36 publications

References 25 publications

Recent Advances onα‐Azidoketones and Esters in the Synthesis ofN‐Heterocycles

Recent Advances onα‐Azidoketones and Esters in the Synthesis ofN‐Heterocycles

Click approach to the novel 1,2,3-triazolium phosphotungstate organic–inorganic hybrids for the highly promoted synthesis of spirooxindoles

Peanut shell as a green biomolecule support for anchoring Cu2O: a biocatalyst for green synthesis of 1,2,3-triazoles under ultrasonic irradiation

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