- Crystal and molecular structures of two triazole derivatives: 4-Cyclopropyl-4,5-dihydro-1H-1,2,3-triazole and Methyl 1-benzyl-1H-1,2,3- triazole-4-carboxylate
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The molecule in 4-cyclopropyl-4,5-dihydro-1H-1,2,3-triazole (I) is disposed about a mirror plane with the triazole ring lying in the plane and being orthogonal to the cyclopropyl ring. Considerable delocalization of π-electron density within the triazole
- Boechat, Nubia,De L. G. Ferreira, Maria,Bastos, Monica M.,Camilo, Ane L. S.,Wardell, Solange M. S. V.,Wardell, James L.,Tiekink, Edward R. T.
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- Regioselective reduction of 1h-1,2,3-triazole diesters
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Regioselective reactions can play pivotal roles in synthetic organic chemistry. The reduction of several 1-substituted 1,2,3-triazole 4,5-diesters by sodium borohydride has been found to be regioselective, with the C(5) ester groups being more reactive towards reduction than the C(4) ester groups. The amount of sodium borohydride and reaction time required for reduction varied greatly depending on the N(1)-substituent. The presence of a β-hydroxyl group on the N(1)-substituent was seen to have a rate enhancing effect on the reduction of the C(5) ester group. The regioselective reduction was attributed to the lower electron densities of the C(5) and the C(5) ester carbonyl carbon of the 1,2,3-triazole, which were further lowered in cases involving intramolecular hydrogen bonding.
- Butler, Christopher R.,Bendesky, Justin,Schoffstall, Allen Milton
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- Magnetic Fe3O4 nanoparticles bearing CuI-NHC complexes by an “auto-click” strategy
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Two copper(I)–NHC complexes bearing an azide group were reacted with alkyne-decorated magnetic Fe3O4 nanoparticles without the use of an external copper source. In the case of the least sterically congested complex, the resulting nan
- Fauché, Kévin,Cisnetti, Federico
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- Tris-isocyanide copper(I) complex enabling copper azide-alkyne cycloaddition in neat conditions
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The three-coordinated homoleptic Cu(I) complex with 2,6-dimethylphenyl isocyanide in the coordination sphere was easily synthesized and isolated as tetrafluoroborate salt. The structure of the compound was determined by single-crystal X-ray diffraction. T
- Ferraro, Valentina,Sole, Roberto,Bortoluzzi, Marco,Beghetto, Valentina,Castro, Jesús
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- Azide-alkyne cycloadditions in a vortex fluidic device: Enhanced "on water" effects and catalysis in flow
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The Vortex Fluidic Device is a flow reactor that processes reactions in thin films. Running the metal-free azide-alkyne cycloaddition in this reactor revealed a dramatic enhancement of the "on water"effect. For the copper-catalyzed azide-alkyne cycloaddit
- Oksdath-Mansilla, Gabriela,Kucera, Renata L.,Chalker, Justin M.,Raston, Colin L.
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supporting information
p. 659 - 662
(2021/01/29)
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- Cu(ii)-alginate-based superporous hydrogel catalyst for click chemistry azide-alkyne cycloaddition type reactions in water
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A novel sustainable hydrogel catalyst based on the reaction of sodium alginate naturally extracted from brown algaeLaminaria digitataresidue with copper(ii) was prepared as spherical beads, namely Cu(ii)-alginate hydrogel (Cu(ii)-AHG). The morphology and
- Ablouh, El-Houssaine,Anane, Hafid,Bahsis, Lahoucine,Julve, Miguel,Stiriba, Salah-Eddine,Taourirte, Moha
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p. 32821 - 32832
(2020/09/21)
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- Structure-Based Design, Synthesis, and Biological Evaluation of Triazole-Based smHDAC8 Inhibitors
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Schistosomiasis is a neglected tropical disease caused by parasitic flatworms of the genus Schistosoma, which affects over 200 million people worldwide and leads to at least 300,000 deaths every year. In this study, initial screening revealed the triazole
- Kalinin, Dmitrii V.,Jana, Sunit K.,Pfafenrot, Maxim,Chakrabarti, Alokta,Melesina, Jelena,Shaik, Tajith B.,Lancelot, Julien,Pierce, Raymond J.,Sippl, Wolfgang,Romier, Christophe,Jung, Manfred,Holl, Ralph
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supporting information
p. 571 - 584
(2020/01/24)
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- A ferrocene functionalized Schiff base containing Cu(ii) complex: Synthesis, characterization and parts-per-million level catalysis for azide alkyne cycloaddition
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Atom economy is one of the major factors in developing catalysis chemistry. Using the minimum amount of catalyst to obtain the maximum product yield is of the utmost priority in catalysis, which drives us to use parts-per-million (ppm) levels of catalyst
- Gayen, Firdaus Rahaman,Ali, Abdul Aziz,Bora, Debashree,Roy, Saptarshi,Saha, Supriya,Saikia, Lakshi,Goswamee, Rajib Lochan,Saha, Biswajit
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supporting information
p. 6578 - 6586
(2020/06/08)
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- Flow hydrodediazoniation of aromatic heterocycles
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Continuous flow processing was applied for the rapid replacement of an aromatic amino group with a hydride. The approach was applied to a range of aromatic heterocycles, confirming the wide scope and substituent-tolerance of the processes. Flow equipment was utilized and the process optimised to overcome the problematically-unstable intermediates that have restricted yields in previous studies relying on batch procedures. Various common organic solvents were investigated as potential hydride sources. The approach has allowed key structures, such as amino-pyrazoles and aminopyridines, to be deaminated in good yield using a purely organic-soluble system.
- R?der, Liesa,Nicholls, Alexander J.,Baxendale, Ian R.
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- The azide-alkyne cycloaddition catalysed by transition metal oxide nanoparticles
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Colloidal nanoparticles of Earth-abundant, first-row transition metal oxides and sulfide, namely magnetite (Fe3O4), manganese and cobalt ferrite, (MnFe2O4, CoFe2O4), manganese(ii) oxide (Mn
- Molteni, Giorgio,Ferretti, Anna M.,Trioni, Mario Italo,Cargnoni, Fausto,Ponti, Alessandro
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p. 18049 - 18061
(2019/12/03)
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- Metal-Free Route to Carboxylated 1,4-Disubstituted 1,2,3-Triazoles from Methoxycarbonyl-Modified Vinyl Sulfone
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A metal-free alternative to the regioselective synthesis of carboxylated 1,4-disubstituted 1,2,3-triazoles (1,4-cDTs) has been accomplished. A methoxycarbonyl-substituted vinyl sulfone on reactions with organic azides resulted in the formation of 1,4-cDTs
- Das, Jayanta,Dey, Santu,Pathak, Tanmaya
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- Synthesis and biological evaluation of 1-benzyl-N-(2-(phenylamino)pyridin-3-yl)-1H-1,2,3-triazole-4-carboxamides as antimitotic agents
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A library of 1-benzyl-N-(2-(phenylamino)pyridin-3-yl)-1H-1,2,3-triazole-4-carboxamides (7a–al) have been designed, synthesized and screened for their anti-proliferative activity against some selected human cancer cell lines namely DU-145, A-549, MCF-7 and HeLa. Most of them have shown promising cytotoxicity against lung cancer cell line (A549), amongst them 7f was found to be the most potent anti-proliferative congener. Furthermore, 7f exhibited comparable tubulin polymerization inhibition (IC50 value 2.04 μM) to the standard E7010 (IC50 value 2.15 μM). Moreover, flow cytometric analysis revealed that this compound induced apoptosis via cell cycle arrest at G2/M phase in A549 cells. Induction of apoptosis was further observed by examining the mitochondrial membrane potential and was also confirmed by Hoechst staining as well as Annexin V-FITC assays. Furthermore, molecular docking studies indicated that compound 7f binds to the colchicine binding site of the β-tubulin. Thus, 7f exhibits anti-proliferative properties by inhibiting the tubulin polymerization through the binding at the colchicine active site and by induction of apoptosis.
- Prasad, Budaganaboyina,Lakshma Nayak,Srikanth,Baig, Mirza Feroz,Subba Reddy,Babu, Korrapati Suresh,Kamal, Ahmed
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p. 535 - 548
(2018/11/26)
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- Green methodologies for copper(I)-catalyzed azide-alkyne cycloadditions: A comparative study
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Successful copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) reactions may be achieved by several methods. In this paper, four synthetic protocols were performed for direct comparison of time required for the synthesis, yield, and purity of the 1H-1,
- Trujillo, Marissa,Hull-Crew, Clayton,Outlaw, Andrew,Stewart, Kevin,Taylor, Loren,George, Laura,Duensing, Allison,Tracey, Breanna,Schoffstall, Allen
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- Synthesis of new triazolyl-oxazoline chiral ligands and study of their coordination to Pd(II) metal centers
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We report an improved protocol for the synthesis of TryOx, a family of N,N chiral ligands in which a 1,2,3-triazol-4-yl moiety bears a chiral 2-oxazoline as the substituent in 4 position. TryOxs were successfully employed for the preparation of cationic P
- Scrivanti, Alberto,Sole, Roberto,Bortoluzzi, Marco,Beghetto, Valentina,Bardella, Noemi,Dolmella, Alessandro
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- Self-assembled orthoester cryptands: Orthoester scope, post-functionalization, kinetic locking and tunable degradation kinetics
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Dynamic adaptability and biodegradability are key features of functional, 21st century host-guest systems. We have recently discovered a class of tripodal supramolecular hosts, in which two orthoesters act as constitutionally dynamic bridgeheads. Having previously demonstrated the adaptive nature of these hosts, we now report the synthesis and characterization-including eight solid state structures-of a diverse set of orthoester cages, which provides evidence for the broad scope of this new host class. With the same set of compounds, we demonstrated that the rates of orthoester exchange and hydrolysis can be tuned over a remarkably wide range, from rapid hydrolysis at pH 8 to nearly inert at pH 1, and that the Taft parameter of the orthoester substituent allows an adequate prediction of the reaction kinetics. Moreover, the synthesis of an alkyne-capped cryptand enabled the post-functionalization of orthoester cryptands by Sonogashira and CuAAC "click" reactions. The methylation of the resulting triazole furnished a cryptate that was kinetically inert towards orthoester exchange and hydrolysis at pH > 1, which is equivalent to the "turnoff" of constitutionally dynamic imines by means of reduction. These findings indicate that orthoester cages may be more broadly useful than anticipated, e.g. as drug delivery agents with precisely tunable biodegradability or, thanks to the kinetic locking strategy, as ion sensors.
- L?w, Henrik,Mena-Osteritz, Elena,Von Delius, Max
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p. 4785 - 4793
(2018/06/07)
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- Heterogeneous azide–alkyne cycloaddition in the presence of a copper catalyst supported on an ionic liquid polymer/silica hybrid material
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Heterogeneous copper catalysts were prepared by the deposition of CuI on a hybrid material consisting of silica and a polymer with imidazolium moieties. The solid materials were characterised using solid-phase NMR, Fourier transform infrared, Raman and X-
- Fehér, Klaudia,Nagy, Enik?,Szabó, Péter,Juzsakova, Tatjána,Srankó, Dávid,G?m?ry, ágnes,Kollár, László,Skoda-F?ldes, Rita
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- Catalytic Intermolecular Cross-Couplings of Azides and LUMO-Activated Unsaturated Acyl Azoliums
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An example for the catalytic synthesis of densely functionalized 1,2,3-triazoles through a LUMO activation mode has been developed. The protocol is enabled by intermolecular cross-coupling reactions of azides with in situ-generated α,β-unsaturated acyl az
- Li, Wenjun,Ajitha, Manjaly J.,Lang, Ming,Huang, Kuo-Wei,Wang, Jian
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p. 2139 - 2144
(2017/08/14)
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- Dual roles of substituted thiourea as reductant and ligand in CuAAC reaction
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A highly efficient catalytic system, CuSO4·5H2O/1-(4-methoxyphenyl)-3-phenylthiourea, for the copper(I)-catalyzed azide–alkyne cycloaddition reaction (CuAAC) was discovered. In the above catalytic system, substituted thiourea acts both as a reductant and a ligand. CuSO4·5H2O/1-(4-methoxyphenyl)-3-phenylthiourea is both an economical and efficient catalyst for the CuAAC reaction. In addition, the new catalytic system has advantageous features including mild and green reaction conditions, and broad substrate compatibility. A variety of 1,4-disubstituted 1,2,3-triazoles have been prepared with good to excellent yields with the CuSO4·5H2O/1-(4-methoxyphenyl)-3-phenylthiourea catalytic system in aqueous solution.
- Wang, Siyu,Jia, Kai,Cheng, Jiajia,Chen, Yu,Yuan, Yaofeng
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p. 3717 - 3721
(2017/09/01)
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- NNN-pincer-copper complex immobilized on magnetic nanoparticles as a powerful hybrid catalyst for aerobic oxidative coupling and cycloaddition reactions in water
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A simple and reliable methodology is described for preparing the first heterogeneous NNN-pincer-copper hybrid catalyst with a high control over surface composition. The strategy relies on the covalently bonding of 2-aminopyridine to cyanuric chloride-functionalized magnetic nanoparticles followed by complexation with CuI. These claims are confirmed by different characterization methods such as SEM, TEM, FT-IR, TGA, ICP, XRD, and elemental analysis. The finely engineered supported catalyst is employed in the aerobic oxidative coupling of terminal alkynes and click reaction using only 0.38 and 0.04 mol% catalyst, respectively. All reactions perform under solvent-free condition or green solvent H2O. Also, the catalyst is readily recovered and reused for up to 8 and 6 subsequent runs in click and homocoupling reactions without significant loss of activity or leaching.
- Zohreh, Nasrin,Jahani, Mahboobeh
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p. 117 - 129
(2016/12/07)
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- Catalytic cyclization of 2,3-dibromopropionates with benzyl azides to afford 1-benzyl-1,2,3-triazole-4-carboxylate: The use of A nontoxic bismuth catalyst
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We synthesized 1,2,3-triazoles via the cyclization of 2,3-dibromopropionates with benzyl azides. Bismuth chloride is an efficient catalyst, and the reaction is accelerated by weak bases such as sodium acetate. A variety of functional groups are compatible
- Sun, Hong-Bin,Li, Dong,Xie, Weiping,Deng, Xinlin
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p. 423 - 430
(2016/04/19)
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- Immobilized copper(II) on nitrogen-rich polymer-entrapped Fe3O4 nanoparticles: A highly loaded and magnetically recoverable catalyst for aqueous click chemistry
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A heterogeneous magnetic copper catalyst was prepared via anchoring of copper sulfate onto multi-layered poly(2-dimethylaminoethyl acrylamide)-coated magnetic nanoparticles and was characterized using various techniques. The catalyst was found to be active, effective and selective for one-pot three-component reaction of alkyl halide, sodium azide and alkyne, known as copper-catalyzed click synthesis of 1,2,3-triazoles. As little as 0.3 mol% of catalyst was found to be effective under the optimum conditions. The catalyst could also be recycled and reused up to seven times without significant loss of activity. Thermal stability, high loading level of copper on catalyst, broad diversity of alkyl/benzyl/allyl bromide/chloride and alkyl/aryl terminal alkynes without isolation of azide intermediate, and good to excellent yields of products make this procedure highly economical.
- Zohreh, Nasrin,Hosseini, Seyed Hassan,Pourjavadi, Ali,Bennett, Craig
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- An efficient and recyclable thiourea-supported copper(i) chloride catalyst for azide-alkyne cycloaddition reactions
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A reaction between two equivalents of bulky thiourea, i.e., 1,3-bis(2,6-dimethylphenyl)thiourea (L) [L = (ArNH)2C = S; Ar = 2,6-Me2C6H3], and CuCl2 or CuCl in THF solvent afforded a bulky thiourea-sta
- Barman, Milan Kr.,Sinha, Ashish Kumar,Nembenna, Sharanappa
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p. 2534 - 2541
(2016/05/19)
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- Bi- and trinuclear copper(I) complexes of 1,2,3-triazole-tethered NHC ligands: Synthesis, structure, and catalytic properties
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A series of copper complexes (3-6) stabilized by 1,2,3-triazole-tethered N-heterocyclic carbene ligands have been prepared via simple reaction of imidazolium salts with copper powder in good yields. The structures of bi- and trinuclear copper complexes we
- Gu, Shaojin,Du, Jiehao,Huang, Jingjing,Xia, Huan,Yang, Ling,Xu, Weilin,Lu, Chunxin
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p. 863 - 873
(2016/07/06)
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- Pressure-accelerated azide-alkyne cycloaddition: Micro capillary versus autoclave reactor performance
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Pressure effects on regioselectivity and yield of cycloaddition reactions have been shown to exist. Nevertheless, high pressure synthetic applications with subsequent benefits in the production of natural products are limited by the general availability o
- Borukhova, Svetlana,Seeger, Andreas D.,Nol, Timothy,Wang, Qi,Busch, Markus,Hessel, Volker
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p. 504 - 512
(2015/03/04)
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- Direct access to 1,4-disubstituted 1,2,3-triazoles through organocatalytic 1,3-dipolar cycloaddition reaction of α,β-unsaturated esters with azides
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DBU-catalyzed organocatalytic 1,3-dipolar cycloaddition reactions of α,β-unsaturated esters with azides have been developed. This strategy generates 1,4-disubstituted 1,2,3-triazoles in high yields with high regioselectivities. It is demonstrated that some of these products can be transformed into important pharmaceutical agents.
- Li, Wenjun,Zhou, Xiao,Luan, Yepeng,Wang, Jian
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p. 88816 - 88820
(2015/11/09)
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- Copper malonamide complexes and their use in azide-alkyne cycloaddition reactions
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We report a rare example of the malonamide functionality being used as a ligand in copper catalysis. We have ligated a homologous series of these O,O-chelating architectures to copper, investigated their structure and exploited them in azide-alkyne cycloa
- Bent,Mahon,Webster
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p. 10253 - 10258
(2015/06/08)
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- Microwave assisted azide-alkyne cycloaddition reaction using polymer supported Cu(i) as a catalytic species: A solventless approach
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A polymer supported copper(i) composite has been synthesized using a one-step chemical synthesis route under ambient conditions. The resultant material serves as an effective catalyst for a 1,3-dipolar cycloaddition reaction between terminal alkynes and a
- Taher, Abu,Nandi, Debkumar,Islam, Rafique Ul,Choudhary, Meenakshi,Mallick, Kaushik
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p. 47275 - 47283
(2015/06/16)
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- A-21·CuI as a catalyst for Huisgen's reaction: About iodination as a side-reaction
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The polymer-supported catalyst Amberlyst A-21·CuI has found many applications in copper(I)-catalyzed Huisgen's (CuAAC) and other reactions. This catalyst was found to be efficient and reusable for the formation of 1,4-disubstituted 1,2,3-triazoles. It was
- Slimi, Riadh,Kalhor-Monfared, Shiva,Plancq, Baptiste,Girard, Christian
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supporting information
p. 4339 - 4344
(2015/06/22)
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- Oximinoalkylamines as ligands for Cu-assisted azide-acetylene cycloaddition
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Oximinoalkylamines were found to be efficient ligands for acceleration of the CuAAC reaction. 'Mixed' oxime-triazole ligands TzβOx2 and Tz2βOx demonstrate an approximately 10-fold enhanced acceleration effect co
- Semakin, Artem N.,Agababyan, Daniil P.,Kim, Sohee,Lee, Sangyoon,Sukhorukov, Alexey Yu.,Fedina, Ksenia G.,Oh, Jinho,Ioffe, Sema L.
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supporting information
p. 6335 - 6339
(2015/11/16)
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- Polystyrene resin-supported CuI-cryptand 22 complex: A highly efficient and reusable catalyst for three-component synthesis of 1,4-disubstituted 1,2,3-triazoles under aerobic conditions in water
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Polystyrene resin-supported copper(I) iodide-cryptand-22 complex (PS-C22-CuI) was synthesized and characterized by FT-IR, EDX, SEM, XPS, and TG-DTA analysis. This complex was found to be a highly active and robust heterogeneous catalyst for either three-component reaction of organic halides, sodium azide, and terminal alkynes, or the reaction of organic azides and alkynes to form 1,4-disubstituted 1,2,3-triazoles in good to excellent yields at room temperature, using water as the green solvent. The catalyst can be not only easily isolated from the final product by filtration but also reused without significant loss of catalytic activity.
- Movassagh, Barahman,Rezaei, Nasrin
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p. 8885 - 8892
(2015/03/04)
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- Microwave-assisted azide-alkyne cycloaddition in water using a heterogeneous Cu-catalyst
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Several triazoles have been synthesized. They were obtained by a Cu-catalyzed cycloaddition of azides and alkynes. The reaction takes place in aqueous media under microwave irradiation using a copper catalyst based on porous glass. The products have been
- Jacob, Katharina,Stolle, Achim
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p. 1251 - 1257
(2014/04/17)
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- Design, synthesis, and antiviral activity of new 1H-1,2,3-triazole nucleoside ribavirin analogs
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Ribavirin is a broad antiviral compound with demonstrated activity against herpes simplex virus (HSV), human immunodeficiency virus HIV-1, influenza virus, respiratory syncytial virus, and hepatitis C virus, among other viruses. However, routine clinical use of ribavirin is limited because this compound is considerably cytotoxic. Herein, we describe the design, synthesis, and antiviral activity of new nucleoside ribavirin analogs based on the following: (1) ring bioisosterism of a 1,2,4-triazole for a 1,2,3-triazole; (2) amide group exchange for other substituents, such as c-propyl, methyl carboxylate, or trifluoromethyl groups; and (3) the ribofuranose remained linked to the triazole ring. Compounds 5a-c were obtained with yields of 65-36 % and tested against Influenza A and HSV-1 replication as well as reverse transcriptase (RT) from human immunodeficiency virus type 1 (HIV-1 RT). Compound 5b (R = CO 2CH3) was the most effective analog, with IC50 values 14 and 3.8 μM for Influenza A and HIV-1 RT, respectively.
- De Lourdes G. Ferreira, Maria,Pinheiro, Luiz C. S.,Santos-Filho, Osvaldo A.,Pecanha, Marta D. S.,Sacramento, Carolina Q.,Machado, Viviane,Ferreira, Vitor F.,Souza, Thiago Moreno L.,Boechat, Nubia
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p. 1501 - 1511
(2014/03/21)
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- Magnetic nanoparticles entrapped in the cross-linked poly(imidazole/imidazolium) immobilized Cu(ii): An effective heterogeneous copper catalyst
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Anchoring of copper sulfate in layered poly(imidazole-imidazolium) coated magnetic nanoparticles provided a highly stable, active, reusable, high loading, and green catalyst for the click synthesis of 1,2,3-triazoles via a one-pot cycloaddition of alkyl h
- Pourjavadi, Ali,Hosseini, Seyed Hassan,Zohreh, Nasrin,Bennett, Craig
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p. 46418 - 46426
(2014/12/10)
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- Synthesis of 1,4-disubstituted 1,2,3-triazoles via click reaction in micro flow reactor
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A Cu (I)-catalyzed three-component click reaction of alkyl bromide, terminal alkyne and sodium azide was developed in micro flow reactor. Sodium ascorbate was added as additive to prevent the oxidative coupling of desired product with terminal alkyne. Und
- Lei, Ming,Hu, Ruijun,Wang, Yanguang,Zhang, Hong
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p. 1511 - 1517
(2016/11/15)
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- Alkyne-azide cycloaddition catalyzed by a dinuclear copper(I) complex
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A novel dinuclear copper complex CuI2(pip)2 was used as a catalyst for alkyne-azide cycloaddition (CuAAC) reaction. High yields (95-99%) were obtained for various substrates at a low loading of 0.2 mol %. The unique struct
- Chen, Hong-Bin,Abeyrathna, Nawodi,Liao, Yi
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supporting information
p. 6575 - 6576
(2015/01/16)
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- An abnormal N-heterocyclic carbene-copper(I) complex in click chemistry
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Herein we report the synthesis of a copper(I) chloro complex using an abnormal N-heterocyclic carbene (aNHC) salt, 1,3-bis(2,6-diisopropylphenyl)-2,4- diphenylimidazolium. The Cu(aNHC) complex efficiently catalyzed Huisgen 1,3-dipolar cycloaddition reacti
- Sau, Samaresh Chandra,Roy, Sudipta Raha,Sen, Tamal K.,Mullangi, Dinesh,Mandal, Swadhin K.
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p. 2982 - 2991
(2014/03/21)
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- 2-Ethynylpyridine-Promoted Rapid Copper(I) Chloride Catalyzed Azide-Alkyne Cycloaddition Reaction in Water
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The copper(I) chloride catalyzed reaction of azides with alkynes in water at room temperature was promoted by the addition of a catalytic amount of 2-ethynylpyridine, affording the corresponding 1,4-disubstituted 1,2,3-triazoles in good yields after a specific reaction time. The catalytic system could be successfully applied to electron-rich, electron-poor, and sterically crowded substrates. A study of the additive effect of pyridine derivatives revealed that alkynyl and 2-pyridyl groups were essential for activating the copper catalyst. Georg Thieme Verlag Stuttgart · New York.
- Hiroki, Hidekatsu,Ogata, Kenichi,Fukuzawa, Shin-Ichi
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p. 843 - 846
(2013/05/22)
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- [Cu8(μ8-H){S2P (OEt)2} 6](PF6): A novel catalytic hydride-centered copper cluster for azide-alkyne cycloaddtion
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A hydride-centered dithiophosphate cluster [Cu8(μ 4-H){S2P(OEt)2}6](PF6) (1)] previously developed by us was applied as a new catalyst to the 1,3-dipolar cycloaddition of organic azides and
- Lee, Bo-Han,Wu, Cheng-Chieh,Fang, Xuan,Liu,Zhu, Jia-Liang
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p. 572 - 577
(2013/07/11)
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- Preparation of Cu(OAc)2/MCM-41 catalyst and its application in the one-pot synthesis of 1,2,3-triazoles in water
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An efficient one-pot synthesis of 1,2,3-triazoles via the three-component coupling reaction between benzyl or alkyl bromides, terminal alkynes, and sodium azide in the presence of catalytic amounts of Cu(OAc)2/MCM-41 catalyst has been described
- Hosseinzadeh, Rahman,Sepehrian, Hamid,Shahrokhi, Farshid
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p. 415 - 421
(2012/10/29)
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- Debenzylation of functionalized 4- and 5-substituted 1,2,3-triazoles
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A range of 4- and 5-substituted N-benzyl-1,2,3-triazoles have been submitted to debenzylation using Pd/C and hydrogen in the presence of 1,1,2-trichloroethane. Triazoles with oxygen-containing substituents are efficiently debenzylated under these conditio
- Farooq, Tahir,Sydnes, Leiv K.,Toernroos, Karl W.,Haug, Bengterik
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experimental part
p. 2070 - 2078
(2012/08/07)
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- Unusual Cu(I)-catalyzed 1,3-dipolar cycloaddition of acetylenic amides: Formation of bistriazoles
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C-carbamoyl-1,2,3-triazoles have recently attracted much interest due to their potent biological activity. While synthesizing C-carbamoyl-1,2,3-triazoles by the copper(I)-catalyzed 1,3-dipolar cycloaddition of organic azides 1 and acetylenic amides 2, we
- Kwon, Mihyun,Jang, Yujin,Yoon, Sunyoung,Yang, Dongsik,Jeon, Heung Bae
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experimental part
p. 1606 - 1609
(2012/04/17)
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- A copper(I) isonitrile complex as a heterogeneous catalyst for azide-alkyne cycloaddition in water
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A structurally well-defined copper(I) isonitrile complex is shown to be an efficient, heterogeneous catalyst for the Huisgen azide-alkyne 1,3-dipolar cycloaddition under mild conditions in water. Notably, this catalyst can also be utilized in a three-component reaction of halides, sodium azide and alkynes to form 1,4-disubstituted 1,2,3-triazoles in high yields. Furthermore, it can be readily recovered by precipitation and filtration and recycled for at least five runs without significant loss of activity.(Figure Presented)
- Liu, Meina,Reiser, Oliver
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p. 1102 - 1105
(2011/04/24)
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- Copper(I) 1,2,3-triazol-5-ylidene complexes as efficient catalysts for click reactions of azides with alkynes
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Complexes of copper with 1,4-diphenyl, 1,4-dimesityl, and 1-(2,6-diisopropylphenyl)-4-(3,5-xylyl)-1,2,3-triazol-5-ylidene (abnormal NHC = N-heterocyclic carbene) were prepared by consecutive treatment of the corresponding azolium salts with silver oxide and copper chloride. The new CuCl(aNHC) complexes efficiently catalyzed click reactions of azides with alkynes to give 1,4-substituted 1,2,3-triazoles in excellent yields at room temperature with short reaction times. CuCl(TPh) was particularly effective for the reaction between sterically hindered azides and alkynes.
- Nakamura, Tatsuhito,Terashima, Takahiro,Ogata, Kenichi,Fukuzawa, Shin-Ichi
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supporting information; experimental part
p. 620 - 623
(2011/04/15)
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- Effects of a flexible alkyl chain on a ligand for CuAAC reaction
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Imidazole derivatives substituted by a normal alkyl group are shown to be efficient as a ligand for the copper(Δ)-catalyzed azide-alkyne cycloaddition (CuAAC) reaction. An alkyl chain on the imidazole ligands shows an efficient steric effect and benefits the reaction. Such functionalities of an alkyl chain allow a rapid CuAAC reaction of even a bulky alkyne, which has been difficult to perform under conventional conditions.
- Asano, Keisuke,Matsubara, Seijiro
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supporting information; experimental part
p. 4988 - 4991
(2010/12/25)
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- On the reactivity of activated alkynes in copper and solvent-free Huisgens reaction
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Terminal alkynes substituted by a carbonyl-type electron-withdrawing group have been found to undergo Huisgens cycloaddition with azides at room temperature in a solvent-free manner; without a need of either heating or catalysis. Metallic salts, other tha
- Elamari, Hichem,Jlalia, Ibtissem,Louet, Charlotte,Herscovici, Jean,Meganem, Faouzi,Girard, Christian
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scheme or table
p. 1179 - 1183
(2010/11/02)
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- Cu-Mn bimetallic catalyst for Huisgen [3+2]-cycloaddition
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Cu-Mn spinel oxide catalyst has been investigated for the ligand-free Huisgen [3+2] cycloaddition. The copper(i) species required in the cycloaddition reaction has been stabilized in the tetrahedral site of the spinel without the need of a stabilizing age
- Yousuf, Syed Khalid,Mukherjee, Debaraj,Singh, Baldev,Maity, Sudip,Taneja, Subhash Chandra
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experimental part
p. 1568 - 1572
(2010/12/24)
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- Boronic acid catalysis for mild and selective [3+2] dipolar cycloadditions to unsaturated carboxylic acids
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Herein, the concept of boronic acid catalysis (BAC) for the activation of unsaturated carboxylic acids is applied in several classic dipolar [3 + 2] cycloadditions involving azides, nitrile oxides, and nitrones as partners. These cycloadditions can be used to produce pharmaceutically interesting, small heterocyclic products, such as triazoles, isoxazoles, and isoxazolidines. These cycloadducts are formed directly and include a free carboxylic acid functionality that can be employed for fur-ther transformations, thereby avoiding prior masking or functionalization. In all cases, BAC provides faster reactions, under milder conditions, with much improved product yields and regioselectivities. In some instances, such as triazole formation from the reaction of azides with 2-alkynoic acids, catalysis with ort/io- nitrophenylboronic acid circumvents the undesirable product decarboxylation observed when using thermal activation. By using NMR spectroscopic studies, the boronic acid catalyst was shown to provide activation by a LUMO-lowering effect in the unsaturated carboxylic acid, likely via a monoacylated hemiboronic ester intermediate.
- Zheng, Hongchao,McDonald, Robert,Hall, Dennis G.
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experimental part
p. 5454 - 5460
(2010/09/15)
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- CuO hollow nanostructures catalyze [3 + 2] cycloaddition of azides with terminal alkynes
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CuO hollow nanostructures have been used for the catalytic [3 + 2] cycloaddition of azides with terminal alkynes to provide the products in good yields with high regioselectivity.
- Young Kim, Jee,Chan Park, Ji,Kang, Hyuntae,Song, Hyunjoon,Hyun Park, Kang
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supporting information; experimental part
p. 439 - 441
(2010/04/04)
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- A convenient and efficient synthesis of C-carbamoyl-1,2,3-triazoles from alkyl bromide by a one-pot sequential addition: Conversion of ester to amide using Zr(Ot-Bu)4
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A convenient and efficient one-pot sequence has been developed for the synthesis of C-carbamoyl-1,2,3-triazoles from alkyl bromide using (i) sodium azide, (ii) methyl propiolate and copper iodide, and (iii) amines, zirconium tert-butoxide, and 1-hydroxybe
- Yang, Dongsik,Kwon, Mihyun,Jang, Yujin,Jeon, Heung Bae
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experimental part
p. 3691 - 3695
(2010/08/20)
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- Immobilized CuO hollow nanospheres catalyzed alkyne-azide cycloadditions
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An approach for gram-scale synthesis of uniform Cu2O nanocubes by a one-pot polyol process was used. The CuO hollow nanostructures were prepared by adding aqueous ammonia solutions with Cu2O nanocube colloidal solutions. CuO hollow n
- Kang, Hyuntae,Jung, Hyun Seok,Kim, Jee Young,Park, Ji Chan,Kim, Mijong,Song, Hyunjoon,Park, Kang Hyun
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experimental part
p. 6504 - 6509
(2011/10/13)
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