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Journal articles on the topic 'Cycloaddition 1,3-dipolaire (CuAAC)'

Author: Grafiati

Published: 9 October 2021

Last updated: 30 July 2025

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1

Svete, Jurij, Uroš Grošelj, Franc Požgan, and Bogdan Štefane. "Copper-Catalyzed Azomethine Imine–Alkyne Cycloadditions (CuAIAC)." Synthesis 50, no. 23 (2018): 4501–24. http://dx.doi.org/10.1055/s-0037-1610284.

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Although the first example of copper-catalyzed azomethine imine–alkyne cycloaddition (CuAIAC) was published only a year after the seminal papers of Meldal and Sharpless on Cu-catalyzed azide–alkyne cycloaddition (CuAAC), the CuAIAC reaction has remained overlooked by the synthetic community for almost a decade. Since 2010, however, CuAIAC reaction started to emerge as a promising supplement to the well-known CuAAC reaction. The present review surveys primarily the literature on CuAIAC reaction since 2003. Beside this, azomethine imine–alkyne cycloadditions catalyzed by other metals, selected e

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2

Nakano, Shun, Akihito Hashidzume, and Takahiro Sato. "Quarternization of 3-azido-1-propyne oligomers obtained by copper(I)-catalyzed azide–alkyne cycloaddition polymerization." Beilstein Journal of Organic Chemistry 11 (June 18, 2015): 1037–42. http://dx.doi.org/10.3762/bjoc.11.116.

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3-Azido-1-propyne oligomer (oligoAP) samples, prepared by copper(I)-catalyzed azide–alkyne cycloaddition (CuAAC) polymerization, were quarternized quantitatively with methyl iodide in sulfolane at 60 °C to obtain soluble oligomers. The conformation of the quarternized oligoAP in dilute DMSO-d 6 solution was examined by pulse-field-gradient spin-echo NMR based on the touched bead model.

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3

Yogesh, Kumar, Bahadur Vijay, K. Singh Anil, S. Parmar Virinder, and K. Singh Brajendra. "Microwave-assisted copper azide alkyne cycloaddition (CuAAC) reaction using D-glucose as a better alternative reductant." Journal of Indian Chemical Society Vol. 90, Oct 2013 (2013): 1893–903. https://doi.org/10.5281/zenodo.5792095.

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Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi-110 007. India <em>E-mail </em>: singhbk@chemistry.du.ac.in <em>Manuscript received 17 July 2013, accepted 18 July 2013</em> D-Glucose has been established as a reducing agent for the copper azide alkyne cycloaddition (CuAAC) reactions. Efficacy of this new reductant has been established against various phenyl acetylenes (14 examples) and aryl azides (16 examples). All reactions proceeded smoothly and 1,2,3-triazolyl derivatives (30 examples) were obtained in moderate to excellent yields (68-96%).

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4

Yamasaki, Shota, Yuri Kamon, Linlin Xu, and Akihito Hashidzume. "Synthesis of Dense 1,2,3-Triazole Polymers Soluble in Common Organic Solvents." Polymers 13, no. 10 (2021): 1627. http://dx.doi.org/10.3390/polym13101627.

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Aiming at synthesis of dense 1,2,3-triazole polymers soluble in common organic solvents, a new 3-azido-1-propyne derivative, i.e., t-butyl 4-azido-5-hexynoate (tBuAH), was synthesized and polymerized by copper(I)-catalyzed azide–alkyne cycloaddition (CuAAC) and Huisgen cycloaddition (HC). CuAAC polymerization produced poly(tBuAH) composed of 1,4-disubstituted 1,2,3-triazole units (1,4-units), whereas HC polymerization gave poly(tBuAH) composed of 1,4- and 1,5-disubstituted 1,2,3-triazole units (1,4- and 1,5-units). In HC polymerization, the fraction of 1,4-unit (f1,4) decreased with the permit

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5

Ashok, Dongamanti, Rangu Kavitha, Srinivas Gundu, and Rao Hanumantha. "Microwave-assisted synthesis of new pyrazole derivatives bearing 1,2,3-triazole scaffold as potential antimicrobial agents." Journal of the Serbian Chemical Society 82, no. 4 (2017): 357–66. http://dx.doi.org/10.2298/jsc160205016a.

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A new series of (E)-3-(3-(4-substituted phenyl)-1-phenyl-1H-pyrazol- 4-yl)-1-(2-hydroxy-4-((1-aryl-1H-1-2,3-triazol-4-yl)methoxy)phenyl)- prop-2-en-1-one derivatives was synthesized. The synthesis of the title compounds involved the 1,3-dipolar Cu(I)-catalyzed alkyne?azide cycloaddition (CuAAC) reaction of (E)-3-(3-(4-substituted phenyl)-1-phenyl-1H-pyrazol-4- -yl)-1-(2-hydroxy-4-(prop-2-yn-1-yloxy)phenyl)prop-2-en-1-ones with aromatic azides. The structures were confirmed by NMR, FT-IR, mass and elemental analysis. All the synthesized compounds (6a?j) were evaluated for their antimicrobial ac

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6

Пивоварова, Е. В., К. К. Босов, И. А. Крупнова, Г. Т. Суханов, А. Г. Суханова та Ю. В. Филиппова. "Синтез и СПЕКТРАЛЬНЫЕ ХАРАКТЕРИСТИКИ новоГО полиГЕТЕРОядерноГО СОЕДИНЕНИЯ НА ОСНОВЕ ФУНКЦИОНАЛЬНЫХ ТРИАЗОЛОВ". Южно-Сибирский научный вестник, № 6(58) (31 грудня 2024): 362–68. https://doi.org/10.25699/sssb.2024.58.6.047.

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Реакцией 1,3-диполряного циклоприсоединения между функциональными производными симметричного 1,2,4-триазола: азидсодержащим диполем (3-азидо-1,2,4-триазолом) и ацетиленовым диполярофилом (1-метил-5-проп-2-инилокси-1Н-[1,2,4]триазолом), впервые синтезировано полигетероциклическое соединение, содержащее в единой молекуле два терминальных 1,2,4-триазоловых (симметричных) гетероцикла и один интернальный 1,2,3-триазоловый (вицинальный) цикл. Показано, что исследованная реакция медь-катализируемого азид-алкинового циклоприсоединения (CuAAC) протекает с выбранными объектами в мягких условиях (комнатн

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7

MUPPARAPU, PRAVEEN KUMAR, NAMRATHA VADDIRAJU, and MOHAN KURRA. "Synthesis and in vitro Antimicrobial Screening of Benzofuran-3(2H)-one Linked Geminal bis 1,2,3-Triazole Hybrid Derivatives." Asian Journal of Chemistry 35, no. 10 (2023): 2543–48. http://dx.doi.org/10.14233/ajchem.2023.28036.

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A series of novel hybrid derivatives, 2,2-di(1H-1,2,3-triazol-1-yl)benzofuran-3(2H)-ones, were synthesized from o-hydroxyacetophenones via a two-step process involving sodium azide, iodine and sodium bicarbonate, followed by Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC) in aqueous conditions. These compounds were characterized using 1H NMR, 13C NMR and mass spectra and analyzed in vitro against bacteria (Staphylococcus aureus, Bacillus subtilis, Escherichia coli, Pseudomonas aeruginosa) and fungi (Candida albicans, Aspergillus niger). Compounds 3f, 3h and 3n showed notable antibacterial a

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8

Bahsis, Lahoucine, Hicham Ben El Ayouchia, Hafid Anane, et al. "Clicking Azides and Alkynes with Poly(pyrazolyl)borate-Copper(I) Catalysts: An Experimental and Computational Study." Catalysts 9, no. 8 (2019): 687. http://dx.doi.org/10.3390/catal9080687.

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The synthesis of 1,4-disubstituted-1,2,3-triazoles under a copper(I)-catalyzed azide–alkyne cycloaddition (CuAAC) regime was accomplished in high yields and a regioselective manner by using two homoscorpionate poly(pyrazolyl)borate anions: tris(pyrazolyl)hydroborate (HB(pz)3−) and bis(pyrazolyl)hydroborate (H2B(pz)2−), which stabilized in situ the catalytically active copper (I) center. The [3+2] cycloaddition (32CA) reactions took place under strict click conditions, including room temperature and a mixture of environmentally benign solvents such as water/ethanol in a 1:1 (v/v) ratio. These c

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9

Dioukhane, Khadim, Younas Aouine, Salaheddine Boukhssas, Asmae Nakkabi, Hassane Faraj, and Anouar Alami. "Synthesis and Characterization of a Novel Biheterocyclic -amino Acid Precursor of the Triazole-Tetrazole Type, via the Copper (I) Catalyzed Alkyne-Azide Cycloaddition Reaction (CuAAC)." European Journal of Advanced Chemistry Research 2, no. 2 (2021): 7–15. http://dx.doi.org/10.24018/ejchem.2021.2.2.53.

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In this paper, we describe the regioselective synthesis of a novel tri-heterocyclic compound, a biheterocyclic amino acid precursor, derived from both triazole and tetrazole. The key step of our synthesis approach was the Huigsen 1,3-dipolar cycloaddition reaction, catalyzed by the copper (I) formed in situ by reduction of Cu(II) salts (CuSO4), 5H2O) by sodium ascorbate, and using as dipole the oxazoline azide derivative 4-(azidomethyl)-4-ethyl-2-phenyl-4,5-dihydrooxazole (4) and as dipolarophile 5-(4-methoxyphenyl)-2-(prop-2-yn-1-yl)-2H-tetrazole (3). The Cu(I) catalysis allowed us to carry o

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10

Neumajer, Gábor, Gergő Tóth, Szabolcs Béni, and Béla Noszál. "Novel ion-binding C3 symmetric tripodal triazoles: synthesis and characterization." Open Chemistry 12, no. 1 (2014): 115–25. http://dx.doi.org/10.2478/s11532-013-0351-z.

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AbstractNovel C3 symmetric tripodal molecules were synthesized from cyclohexane 1,3,5-tricarboxylic acid. Utilizing click and Sonogashira reactions, ion-binding triazole and pyridazin-3(2H)-one units were incorporated to form polydentate ligands for ion complexation. The structures of the novel C3 symmetric derivatives were extensively characterized by 1H, 13C and 2D NMR techniques along with HRMS and IR. The copper(I)-binding potentials of these ligands were investigated by using them as additives in model copper(I)-catalysed azide-alkyne cycloaddition (CuAAC) reactions. The copper(I) complex

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11

Sorroza-Martínez, Kendra, Israel González-Méndez, Mireille Vonlanthen та ін. "First Class of Phosphorus Dendritic Compounds Containing β-Cyclodextrin Units in the Periphery Prepared by CuAAC". Molecules 25, № 18 (2020): 4034. http://dx.doi.org/10.3390/molecules25184034.

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A new class of phosphorus dendritic compounds (PDCs) having a cyclotriphosphazene (P3N3) core and decorated with six β-cyclodextrin (βCD) units, named P3N3-[O-C6H4-O-(CH2)n-βCD]6, where n = 3 or 4 was designed, and the synthesis was performed using copper (I) catalyzed alkyne-azide cycloaddition (CuAAC). To obtain the complete substitution of the P3N3, two linkers consisting of an aromatic ring and an aliphatic chain of two different lengths were assessed. We found that, with both linkers, the total modification of the periphery was achieved. The two new obtained dendritic compounds presented

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12

Le, Duc Anh, Ngoc Hung Truong, Van Dung Vu, et al. "Design, Synthesis, and Biological Activity Evaluation of Novel AZT and Adenosine-Derived 1,2,3-Triazoles." Journal of Chemistry 2023 (September 28, 2023): 1–17. http://dx.doi.org/10.1155/2023/1605316.

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CuSO4/hydrazine hydrate was used as a catalyst system for copper(I)-catalyzed alkyne-azide cycloaddition (CuAAC) of AZT and 5′-azido adenosine with terminal alkynes to give 30 novel 1,2,3-triazole derivatives. Screening for their anticancer, anti-inflammatory, angiotensin-converting enzyme 2 (ACE2), and 3C-like protease (3CLpro) inhibitory activities showed that several triazoles of AZT containing murayafoline A and indirubin-3′-oxime inhibited the growth of HepG2 and LU-1 with the IC50 values ranging from 11.01 to 19.87 μg/mL. Besides that, some triazole derivatives of adenosine exhibited ant

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13

Ivanskaya, E. V., M. I. Meschaninova, M. A. Vorobyeva, D. O. Zharkov, and D. S. Novopashina. "The approach to the preparation of cyclic photocleavable RNA for photoactivatable CRISPR/Cas9 System." Биоорганическая химия 50, no. 5 (2024): 622–35. https://doi.org/10.31857/s0132342324050051.

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The development of controllable gene editing systems on the base of CRISPR/Cas is an actually problem of modern molecular biology and genetic enginery. Interesting variant of solution of this problem is modification of guide RNA by introduction of photocleavable linkers. We developed the approach to the synthesis of cyclic photocleavable guide crRNA for the CRISPR/Cas9 system with photolinker on the base of 1-(2-nitrophenyl)-1,2-ethanediol (PL). Upon irradiation by UV-light these guide RNA are linearized and CRISPR/Cas9 system is activated. Two chemical methods to the cyclization of RNA were t

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14

Librando, Ivy L., Abdallah G. Mahmoud, Sónia A. C. Carabineiro, M. Fátima C. Guedes da Silva, Carlos F. G. C. Geraldes, and Armando J. L. Pombeiro. "The Catalytic Activity of Carbon-Supported Cu(I)-Phosphine Complexes for the Microwave-Assisted Synthesis of 1,2,3-Triazoles." Catalysts 11, no. 2 (2021): 185. http://dx.doi.org/10.3390/catal11020185.

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A set of Cu(I) complexes with 3,7-diacetyl-1,3,7-triaza-5-phosphabicyclo-[3.3.1]nonane (DAPTA) phosphine ligands viz. [CuX(κP-DAPTA)3] (1: X = Br; 2: X = I) and [Cu(μ-X)(κP-DAPTA)2]2 (3: X = Br; 4: X = I) were immobilized on activated carbon (AC) and multi-walled carbon nanotubes (CNT), as well as on these materials after surface functionalization. The immobilized copper(I) complexes have shown favorable catalytic activity for the one-pot, microwave-assisted synthesis of 1,2,3-triazoles via the azide-alkyne cycloaddition reaction (CuAAC). The heterogenized systems with a copper loading of only

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15

Canseco-González, Daniel, José Luis Rodríguez de la O, and José Enrique Herbert-Pucheta. "Combined XRD-paramagnetic 13C NMR spectroscopy of 1,2,3-triazoles for revealing copper traces in a Huisgen click-chemistry cycloaddition. A model case." Heterocyclic Communications 25, no. 1 (2019): 98–106. http://dx.doi.org/10.1515/hc-2019-0018.

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AbstractCopper-catalyzed Alkyne-Azide Cycloaddition (CuAAC) click chemistry robustness has been demonstrated over recent years to produce 1,2,3-triazoles with excellent yields at mild conditions with simple purification methods. However, the consequences of having copper paramagnetic traces in final products, which complicate spectroscopic assignments and can produce inaccurate conclusions, has been scarcely discussed. Herein we present a strategy that combines X-Ray Diffraction (XRD) with 13C- paramagnetic Nuclear Magnetic Resonance spectroscopy, in order to demonstrate the presence of parama

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Yang, Yanqiong, Asami Mori, and Akihito Hashidzume. "Emission Properties of Diblock Copolymers Composed of Poly(ethylene glycol) and Dense 1,2,3-Triazole Blocks." Polymers 11, no. 7 (2019): 1086. http://dx.doi.org/10.3390/polym11071086.

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This article describes a new block copolymer (EGm-b-APn, where m and n denote the degrees of polymerization) of poly(ethylene glycol) (PEG) and poly(1,4-(1-H-1,2,3-triazolylene)methylene) prepared by copper(I)-catalyzed azide–alkyne cycloaddition (CuAAC) polymerization of 3-azido-1-propyne (AP) in the presence of PEG carrying a propargyl moiety. The EGm-b-APn samples are well soluble in polar organic solvents. Unexpectedly, we observed that solutions of EGm-b-APn in N,N-dimethylformamide emitted fluorescence. We systematically studied absorption and emission properties of the block copolymers.

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17

Figueredo, Andreza S., Peterson de Andrade, Thalita B. Riul, et al. "Galactosyl and sialyl clusters: synthesis and evaluation against T. cruzi parasite." Pure and Applied Chemistry 91, no. 7 (2019): 1191–207. http://dx.doi.org/10.1515/pac-2019-0216.

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AbstractThe multivalent effect of carbohydrates (glycoclusters) has been explored to study important biological targets and processes involvingTrypanosoma cruzi(T. cruzi) infection. Likewise, CuAAC cycloaddition reactions (click chemistry) have been applied as useful strategy in the discovery of bioactive molecules. Hence, we describe the synthesis of 1,2,3-triazole-based tetravalent homoglycoclusters (1–3) and heteroglycoclusters (4and5) ofd-galactopyranose (C-1 and C-6 positions) and sialic acid (C-2 position) to assess their potential to inhibitT. cruzicell invasion and also its cell surfac

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18

Wang, Yu, Yudong Wang, Sushant Sahu, August A. Gallo, and Xiao-Dong Zhou. "Efficient Synthesis of High-Performance Anion Exchange Membranes by Applying Clickable Tetrakis(dialkylamino)phosphonium Cations." Polymers 15, no. 2 (2023): 352. http://dx.doi.org/10.3390/polym15020352.

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Tetrakis(dialkylamino)phosphonium (TKDAAP) compounds exhibit extraordinary base resistance, a prerequisite feature for high-performance anion exchange membranes (AEMs). It is, however, challenging to synthesize a TKDAAP compound with reactive functionality that can be used to link the cation to a polymer backbone. In this study, two TKDAAP compounds with alkyne functionality were synthesized and incorporated into an azide-modified SBS triblock copolymer backbone via Cu(I)-catalyzed alkyne–azide cycloaddition (CuAAC) “click” chemistry. The properties of the resulting AEMs were characterized. It

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19

Pucci, Alessandra, Gianluigi Albano, Matteo Pollastrini, et al. "Supported Tris-Triazole Ligands for Batch and Continuous-Flow Copper-Catalyzed Huisgen 1,3-Dipolar Cycloaddition Reactions." Catalysts 10, no. 4 (2020): 434. http://dx.doi.org/10.3390/catal10040434.

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The lack of supported versions of the tris[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl]amine (TBTA) ligand, suitable for flow-chemistry applications at scale, prompted us to develop a new route for the immobilization of such tris-triazole chelating units on highly cross-linked polystyrene resins. With this aim, the preparation of the known TBTA-type monomer 3 was optimized to develop a high-yield synthetic sequence, devoid of chromatographic purifications at any stage. Then, bead-type (P7) and monolithic (M7) functional resins were obtained by the easy and scalable suspension- or mold-copolymerizat

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20

Tale, Rajesh H., Venkatesh B. Gopula, and Gopal K. Toradmal. "‘Click’ ligand for ‘click’ chemistry: (1-(4-methoxybenzyl)-1-H-1,2,3-triazol-4-yl)methanol (MBHTM) accelerated copper-catalyzed [3+2] azide–alkyne cycloaddition (CuAAC) at low catalyst loading." Tetrahedron Letters 56, no. 43 (2015): 5864–69. http://dx.doi.org/10.1016/j.tetlet.2015.09.010.

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21

Drozd, Natalia, Alexey Lunkov, Balzhima Shagdarova, Alla Il’ina, and Valery Varlamov. "New N-Methylimidazole-Functionalized Chitosan Derivatives: Hemocompatibility and Antibacterial Properties." Biomimetics 8, no. 3 (2023): 302. http://dx.doi.org/10.3390/biomimetics8030302.

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Novel imidazole derivatives of the low molecular weight chitosan N-(2-hydroxypropyl)-1H-1,2,3-triazol-4-yl)methyl)-1-methyl-1H-imidazol-3-ium chitosan chloride (NMIC) were synthesized using copper-catalyzed azide–alkyne cycloaddition (CuAAC). The degrees of substitution (DSs) for the new derivatives were 18–76%. All chitosan derivatives (2000 µg/mL) were completely soluble in water. The antimicrobial activity of the new compounds against E. coli and S. epidermidis was studied. The effect of chitosan derivatives on blood and its components was studied. NMIC samples (DS 34–76%) at a concentratio

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22

Victor, Mauricio M., Ravir R. Farias, Danielle L. da Silva, et al. "Synthesis and Evaluation of Antifungal and Antitrypanosomastid Activities of Symmetrical 1,4-Disubstituted-1,2,3-Bistriazoles Obtained by CuAAC Conditions." Medicinal Chemistry 15, no. 4 (2019): 400–408. http://dx.doi.org/10.2174/1573406414666181024111522.

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Background: The trypanosomatids, such as the protozoan Leishmania spp., have a demand by ergosterol, which is not present in the membrane from mammal cells. The suppression of the synthesis of ergosterol would be a new target of compounds with leishmanicidal activity, and bistriazole has shown trypanocidal activity by this mechanism. The incidence of fungal infections has increased at an alarming rate over the last decades. This is related both to the growing population of immune-compromised individuals and to the emergence of strains that are resistant to available antifungals. Therefore, the

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23

Tale, Rajesh H., Venkatesh B. Gopula, and Gopal K. Toradmal. "ChemInform Abstract: ′Click′ Ligand for ′Click′ Chemistry: (1-(4-Methoxybenzyl)-1-H-1,2,3-triazol-4-yl)methanol (MBHTM) Accelerated Copper-Catalyzed [3 + 2] Azide-Alkyne Cycloaddition (CuAAC) at Low Catalyst Loading." ChemInform 47, no. 15 (2016): no. http://dx.doi.org/10.1002/chin.201615136.

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Brylev, Vladimir A., Ekaterina V. Ryabukhina, Ekaterina V. Nazarova, et al. "Towards Aptamer-Targeted Drug Delivery to Brain Tumors: The Synthesis of Ramified Conjugates of an EGFR-Specific Aptamer with MMAE on a Cathepsin B-Cleavable Linker." Pharmaceutics 16, no. 11 (2024): 1434. http://dx.doi.org/10.3390/pharmaceutics16111434.

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Background/Objectives: Targeted delivery of chemotherapeutic agents is a well-established approach to cancer therapy. Antibody–drug conjugates (ADCs) typically carry toxic payloads attached to a tumor-associated antigen-targeting IgG antibody via an enzyme-cleavable linker that releases the drug inside the cell. Aptamers are a promising alternative to antibodies in terms of antigen targeting; however, their polynucleotide nature and smaller size result in a completely different PK/PD profile compared to an IgG. This may prove advantageous: owing to their lower molecular weight, aptamer-drug co

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Saraiva, Nuno M., Ana Alves, Ana Isabel Barbosa, et al. "Click on Click: Click-Flavone Glycosides Encapsulated in Click-Functionalised Polymersomes for Glioblastoma Therapy." Pharmaceutics 17, no. 6 (2025): 771. https://doi.org/10.3390/pharmaceutics17060771.

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In this study, three new 3,7-dihydroxyflavone (1) derivatives with different sugars were designed and synthesised by click chemistry. Click chemistry requires the previously modification of building blocks with azide and alkyne groups and therefore, the 3,7-dihydroxyflavone (1) was first converted in 3,7-(prop-2-yn-yloxy)flavone (2) and acetobromo-α-D-glucose (3) was converted into 2,3,4,6-tetra-O-acetyl-β-glucopyranosyl azide (4). Subsequently, a click reaction was performed via copper-catalysed cycloaddition (CuAAC) between 2 and 4, as well as between 2 and 2-acetamido-3,4,6-tetra-O-acetyl-2

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Santos, Fabíola Suelen dos, Rossimiriam Pereira de Freitas, Camila Simões de Freitas, et al. "Synthesis of 1,2,3-Triazole-Containing Methoxylated Cinnamides and Their Antileishmanial Activity against the Leishmania braziliensis Species." Pharmaceuticals 16, no. 8 (2023): 1113. http://dx.doi.org/10.3390/ph16081113.

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Leishmaniasis is a group of infectious diseases caused by protozoan parasites that belong to the genus Leishmania. Currently, there is no human vaccine, and the available treatments are associated with toxicity, high cost, and the emergence of resistant strains. These factors highlight the need to identify new antileishmanial candidates. In this study, we synthesized twenty-four methoxylated cinnamides containing 1,2,3-triazole fragments and evaluated their antileishmanial activity against the Leishmania braziliensis species, which is the main etiological agent responsible for American Tegumen

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Ahabchane, Noureddine Hamou, Abdoulaye Keïta, and El Mokhtar Essassi. "Synthèse des 1 -pyrazolyl, isoxazolyl et 1,2,3-triazolylméthyl-1,5-benzodiazépines par cycloaddition dipolaire-1,3." Comptes Rendus de l'Académie des Sciences - Series IIC - Chemistry 2, no. 9-10 (1999): 519–23. http://dx.doi.org/10.1016/s1387-1609(00)86437-3.

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28

Govdi, Anastasia I., Natalia Danilkina, Andrey A. Shtyrov, et al. "Cu-Catalyzed Cycloaddition of Aryl Azides to 1-Iodobuta-1,3-diynes: An Experimental and Quantum Chemical Study of Unusual Regiochemistry." New Journal of Chemistry, 2024. http://dx.doi.org/10.1039/d3nj03823h.

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Cu-Catalyzed azide-alkyne cycloaddition (CuAAC) in the case of 1-iodoalkynes has been known as a synthetic tool towards 5-iodo-1,2,3-triazole derivatives. We found that CuAAC of 1-iodobuta-1,3-diynes and aryl azides under CuI(PPh3)3...

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Sahoo, Subham, Rajesh Patra, Tanmay Rom, Avijit Kumar Paul, and Debajit Sarma. "Cu(I) Coordination Polymer‐Catalyzed Azide–Alkyne Cycloaddition Click Reaction at Room Temperature." European Journal of Inorganic Chemistry, November 2, 2023. http://dx.doi.org/10.1002/ejic.202300559.

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Framework based compounds for eco‐friendly catalysis is of utmost industrial interest. Cu(I)‐catalyzed "click" reactions are a class of highly efficient and widely used chemical reactions in organic synthesis for potential applications in biotechnology, medicine, polymer, and material sciences. The importance of click chemistry also acknowledge by 2022 Noble Prize in chemistry. One of the most well‐known Cu(I)‐catalyzed click reactions is the copper‐catalyzed azide‐alkyne cycloaddition (CuAAC), which is a type of Huisgen 1,3‐dipolar cycloaddition reaction. Herein, three stable copper(I)‐coordi

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Shinde, Kshitij Sanjay, Philipp Michael, and Wolfgang H. Binder. "Mechanochemical Activation of A Metal‐Organic Framework (MOF) Embedded Within A Tpu Matrix: Probing Fluorogenic Stress‐Sensing." Macromolecular Chemistry and Physics, September 25, 2023. http://dx.doi.org/10.1002/macp.202300297.

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AbstractWe here report a mechanochemically triggered Cu(I) bis(N‐heterocyclic carbene (NHC))‐based MOF embedded into a thermoplastic polyurethane (TPU)‐matrix. The induced fluorogenic copper‐catalyzed azide‐alkyne cycloaddition (CuAAC) reveals the stressed parts within the thermoplastic PU via a simple optical detection. As determined via oscillating tensile rheology on dumbbell‐shaped samples of TPU, a MOF, containing 4.66% copper, catalyzes the fluorogenic CuAAC between the non‐fluorescent precursor dyes, 8‐azidonaphthalen‐2‐ol and 3‐hydroxyphenylacetylene. After mechanical activation of the

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Burilov, V. A., M. Mailyan, S. E. Solovieva, and I. S. Antipin. "Functional supramolecular systems based on amphiphilic (thia)calix[4]arenes derivatives." Chemical Journal of Armenia, February 6, 2024, 350–74. http://dx.doi.org/10.54503/0515-9628-2023.76.4-350.

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Supramolecular chemistry is one of the most actively developing areas of modern science. The inexhaustible interest in supramolecular structures stems from their ability to self-assemble, that allows to create systems modeling processes occurring in living organisms, as well as to use nature's approaches to create such functional systems as molecular receptors, catalysts, nanoreactors, molecular machines, etc. For this reason, special attention of researchers working in the field of supramolecular chemistry is focused on amphiphilic molecules which are able to form highly ordered molecular ens

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Bucevičius, Jonas, and Sigitas Tumkevičius. "2,4-Diazidopyrrolo[2,3-d]pyrimidines: synthesis, ring–chain tautomerism and Cu(I)-catalyzed azide–alkyne cycloaddition reaction." Chemija 26, no. 2 (2015). https://doi.org/10.6001/chemija.2015.26.2.9.

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2,4-Diazidopyrrolo[2,3-d]pyrimidines were synthesized by the reaction of the corresponding 2,4-dichloropyrrolo[2,3-d]pyrimidines with sodium azide at room temperature. 2,4-Diazidopyrrolo[2,3-d]pyrimidines were shown to exist in an equilibrium with the corresponding 5-azidopyrrolo[3,2-e]tetrazolo[1,5-c]pyrimidine. The proportion of the tetrazole tautomer increases with increasing solvent polarity. The CuAAC reaction of the obtained azides with 3-methylphenyl- and 4-biphenylylethynes afforded the corresponding 2,4-bis(4-aryl-1,2,3-triazol-1-yl)pyrrolo[2,3-d]pyrimidines.

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Zhou, Yingqing, Yanping Xu, Xiuzhe Yin, et al. "Synthesis of Dendronized Polymers via a “m+n” Grafting‐onto Strategy with Reaction‐Enhanced Reactivity of Intermediates (RERI) Mechanism." Chinese Journal of Chemistry, January 18, 2025. https://doi.org/10.1002/cjoc.202401233.

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Comprehensive SummaryDendronized polymers (DenPols) with tunable shape and surface property have been recognized as a type of promising unimolecular nanomaterials. However, it still has lacked a rapid and efficient approach to the facile synthesis of DenPols with high‐generation and well‐defined structures. Herein, we report a “m+n” grafting‐onto strategy combined with the copper‐catalyzed azide‐alkyne cycloaddition (CuAAC) reaction with reaction‐enhanced reactivity of intermediates (RERI) mechanism for synthesizing DenPols Gm+n by attaching n‐generation dendrons (Gn) onto the m‐generation Den

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Sinozaki, Yuki, Ryota Otani, Hiroki Tanimoto, and Takenori Tomohiro. "Synthesis and Application of Azide‐Incorporated Copper‐Chelating Peptides for Efficient Click Conjugation Reaction." Journal of Heterocyclic Chemistry, May 27, 2025. https://doi.org/10.1002/jhet.4955.

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ABSTRACTBioorthogonal reactions that rapidly generate stable products in water are powerful tools for the functionalization and analysis of biomolecules of interest. Here, we developed a series of water‐soluble copper‐chelating azides for rapid copper‐catalyzed azide‐alkyne [3+2] cycloaddition (CuAAC) reactions. The integrated accelerating ligand, in which introduced an azido group via a linker to a histidine‐ and methionine‐containing peptide, rapidly and quantitatively afford the triazole product. In the application to protein labeling, the apparent rate constant was approximately three orde

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Peng, Lifen, Jiayi Chen, Yi Chen, et al. "Sulfur‐containing 1,2,3‐triazoles: synthesis and properties." European Journal of Organic Chemistry, December 15, 2023. http://dx.doi.org/10.1002/ejoc.202301146.

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Sulfur‐containing 1,2,3‐triazoles display bioactivities like antidepressant, antifungal activity, antitumor, etc. Numerous approaches have been established to form sulfur‐containing 1,2,3‐triazoles. 4‐Sulfanyl‐ and 5‐ sulfanyl‐1,2,3‐triazoles were produced by metal‐catalyzed azide‐alkyne cycloaddition (AAC), etc. N‐Sulfonyl‐1,2,3‐triazoles were generated via the reaction of acetylides with sulfonyl azides, CuAAC. 4‐Sulfonyl‐1,2,3‐triazoles were produced through [3+2] cycloaddition and reaction of azide with bromovinylsulfonyl fluoride. Although 5‐sulfonyl‐1,2,3‐triazoles were formed successful

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Akacha, Rania, Imen Abdelhedi-Miladi, Damien Montarnal, Hatem Ben Romdhane, and Eric Drockenmuller. "Trans‐N‐alkylation Covalent Exchanges on 1,3,4‐Trisubstituted 1,2,3‐Triazolium Iodides." European Journal of Organic Chemistry, September 14, 2023. http://dx.doi.org/10.1002/ejoc.202300587.

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1,3,4‐Trisubstituted 1,2,3‐triazolium salts having either aliphatic or benzylic substituents at the N‐1 and N‐3 positions were synthesized in two steps involving: i) copper(I) catalyzed azide‐alkyne 1,3‐dipolar cycloaddition (CuAAC), and ii)N‐alkylation of the 1,2,3‐triazole intermediates. Trans‐N‐alkylation reactions in bulk and in the presence of excess methyl iodide were monitored by 1H NMR spectroscopy for each 1,2,3‐triazolium molecular model. By assigning the different formed species and their respective evolution with time, it was possible to conclude that trans‐N‐alkylation exchange re

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Evangelista, Roberta, Larissa Pereira, Luciana de Souza, et al. "Synthesis and Evaluation of the Antileishmanial Activity of Novel Eugenol Analogs Containing 1,2,3-Triazole Fragments Against Intracellular Leishmania braziliensis." Journal of the Brazilian Chemical Society, 2023. http://dx.doi.org/10.21577/0103-5053.20230073.

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This investigation describes the synthesis of eugenol analogs presenting 1,2,3-triazole fragments and evaluation of their antileishmanial activity. The alkylation of guaiacol (1) with allyl bromide afforded 1-(allyloxy)-2-methoxybenzene (2) (93% yield). The Claisen rearrangement conducted with 1 gave ortho eugenol (3) (82% yield). Alkylation procedures performed with 3 produced 1-allyl-3-methoxy-2-(prop-2-yn-1-yloxy)benzene (4) (73% yield) and 1-allyl-3-methoxy-2-(pent4-yn-1-yloxy)benzene (6) (53% yield). The copper(I)-catalyzed alkyne-azide cycloaddition (CuAAC) reactions involving alkynes 4

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Dias, Maria, Bianca de Sousa, Marisa Ionta, et al. "Synthesis of 1,2,3-Triazole Benzophenone Derivatives and Evaluation of in vitro Sun Protection, Antioxidant Properties, and Antiproliferative Activity on HT-144 Melanoma Cells." Journal of the Brazilian Chemical Society, 2021. http://dx.doi.org/10.21577/0103-5053.20200211.

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Benzophenones display several biological activities, including antioxidant, anticancer, and photoprotective. Furthermore, antioxidants can minimize both ultraviolet absorption and tumor development. In the present investigation, a series of twenty-six 1,2,3-triazole-benzophenone derivatives were synthesized and had their antioxidant, anticancer, and photoprotective effects evaluated. For the compounds synthesis, 4,4’-dihydroxybenzophenone (1a) and 2,4-dihydroxybenzophenone (1b) were propargylated, affording the alkynes bis(4-(prop-2-yn1-yloxy))benzophenone (2a) and (2-hydroxy-4-(prop-2-yn-1-yl

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A. B. Morais, Pedro, Natália A. Guedes, Caroline S. Fontes, et al. "Drug Repurposing Strategy to Develop New AZT Derivatives Targeting SARS‑CoV-2 Mpro: Synthesis, Computational Studies, and Enzymatic Evaluation." Journal of the Brazilian Chemical Society, 2025. https://doi.org/10.21577/0103-5053.20250012.

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This study focused on the synthesis and inhibitory activity of AZT (3’-azido-3’-deoxythymidine) 1,2,3-triazole derivatives against the main protease of severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2), supported by molecular dynamics. The triazoles were synthesized through CuAAC (copper(I)-catalyzed alkyne-azide cycloaddition) with microwave irradiation. Fourier transform infrared spectroscopy (FTIR), 1 H and 13C NMR (nuclear magnetic resonance) and mass analyses confirmed the structures of 3a-3j. A luminescence assay was carried out to evaluate main protease (Mpro) inhibition. Mol

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sprotocols. "Simple and scalable iodination of 2,6–dialkylanilines: useful building blocks for synthesis." January 4, 2015. https://doi.org/10.5281/zenodo.13724.

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Authors: Houssein Ibrahim, Clémentine Gibard, Audrey Hospital, Christelle Gaulier, Natasha Hewitt, Arnaud Gautier & Federico Cisnetti ### Abstract The syntesis of 2,6-dimethyl-4-iodoaniline and 2,6-diisopropyl-4-iodoanilne is described. Both compounds were easily obtained in using an aromatic iodination reaction with molecular iodine. The desired products were isolated in nearly quantitative yields after a simple extraction. The crude materials are pure according to NMR. ### Introduction 4–iodo–2,6–dialkylanilines are useful building blocks for chemical synthesis as highlighted in several

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