- 1,4-Dihydroxyanthraquinone-copper(II) nanoparticles immobilized on silica gel: A highly efficient, copper scavenger and recyclable heterogeneous nanocatalyst for a click approach to the three-component synthesis of 1,2,3-triazole derivatives in water
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High yielding preparation of structurally different β-hydroxy 1,4-disubstituted 1,2,3-triazole from the regio-selective reaction of epoxides 2a-2c with wide range of terminal alkynes 1a-1j, and sodium azide in the presence of catalytic amount, complexed form of homogeneous catalyst [bis 1,4-mono ester hydroxy anthraquinone copper(II)] (5.0 mol%), [AQ 2Cu(II)] 7 at 25 °C in water has been described. To benefit from the recovery and reuse of the catalyst, a novel heterogeneous nanoparticles of catalyst [bis 1,4-mono ester hydroxy anthraquinone copper(II) aminopropyl silica gel] (5.0 mol%), [AQ2Cu(II)-APSiO2] 13 bearing oxygen anthraquinone ligands with strong copper(II) affinity was easily prepared by using silica gel as a suitable support. The heterogeneous catalyst was fully characterized by XRD, SEM, AFM, ICP, TG methods for analysis of nitrogen adsorption, and FT-IR techniques. The remarkable features of this protocol are high yields, short reaction times, a cleaner reaction profile in an environmentally benign solvent (H2O), one-pot procedure and the method is applicable to large-scale operation without any problem. Furthermore, the catalyst could be recovered and easily removed by simple filtration of the reaction mixture and it was recycled ten times showing negligible copper leaching. In their uncomplexed form of homogeneous catalyst [AQ 2Cu(II)] 7 and heterogeneous catalyst [AQ2Cu(II)- APSiO2] 13, the anthraquinone ligand 6 and [AQ-APSiO2] 12 are very efficient copper scavengers able to catalyze the 1,3-dipolar cycloaddition reaction of azides with alkynes (CuAAC) without pre-synthesis of catalysts.
- Sharghi, Hashem,Khoshnood, Abbas,Doroodmand, Mohammad Mahdi,Khalifeh, Reza
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- 1D Azido bridged Cu(II) coordination polymer with 1,3-oxazolidine ligand as an effective catalyst for green click synthesis of 1,2,3-triazoles
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A new 1D azido bridged Cu(II) coordination polymer with 1,3-oxazolidine based ligand, [Cu(H3L)(μ1,3-N3)(N3)]n (1), was synthesized and characterized by elemental analysis and spectroscopic methods. Th
- Bikas, Rahman,Ajormal, Fatemeh,Noshiranzadeh, Nader,Emami, Marzieh,Kozakiewicz, Anna
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- Asymmetric transfer hydrogenation of heterocycle-containing acetophenone derivatives using N-functionalised [(benzene)Ru(II)(TsDPEN)] complexes
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The application of enantiomerically-pure ruthenium(II) catalysts containing N - functionalised TsDPEN ligand to the asymmetric transfer hydrogenation of 15 examples of α-heterocyclic acetophenone derivatives is reported. Products of up to 99% ee were formed.
- Barrios-Rivera, Jonathan,Xu, Yingjian,Clarkson, Guy J.,Wills, Martin
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- New functionalization of graphene oxide with N2O2 ligand for efficient loading of Cu nanostructures as a heterogeneous nanocatalyst for the synthesis of β-hydroxy-1,2,3-triazoles
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A new and heterogeneous copper complex immobilized on graphene oxide (GO) was prepared. This was achieved through organic functionalization of GO using 1,8-diamino-3,6-dioxaoctane (DADO) and then inorganic coordination of copper on the edges and basal pla
- Rakhshanipour, Mansoureh,Eshghi, Hossein,Bakavoli, Mehdi
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- Visible-light activated metal catalyst-free vicinal diazidation of olefins with sulfonium iodate(i) species
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A visible light-induced vicinal diazidation of various alkenes using stable sulfonium bis(acetoxy)iodate(i) and sodium azide as a radical precursor is described. The trimethylsulfonium [bis(azido)iodate(i)] species, intrinsically generated in situ, demonstrated unprecedented reactivity toward CC π bond-promoting selective azidation under photochemical conditions without any photoredox or metal catalyst. The visible-light stimulated diazidation reaction provides a convenient and straightforward approach to highly prevalent vicinal nitrogen scaffolds of myriad therapeutic importance.
- Reddy, Thurpu Raghavender,Rao, Dodla Sivanageswara,Kashyap, Sudhir
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p. 2833 - 2836
(2019/03/17)
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- Enantioselective separation of (±)-β-hydroxy-1,2,3-triazoles by supercritical fluid chromatography and high-performance liquid chromatography
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This paper reports the enantioseparation of β-hydroxy-1,2,3-triazole derivatives, which present a broad range of biological properties, by supercritical fluid chromatography (SFC) and high-performance liquid chromatography techniques (HPLC). Polysaccharid
- Alvarenga, Natália,Porto, André L.M.,Barreiro, Juliana Cristina
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p. 890 - 899
(2018/04/30)
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- Stereoselective reduction of 2-azido-1-phenylethanone derivatives by whole cells of marine-derived fungi applied to synthesis of enantioenriched β-hydroxy-1,2,3-triazoles
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Several marine-derived fungi were evaluated by the bioreduction of 2-azido-1-phenylethanone 1, and the strains A. sydowii CBMAI 935 and M. racemosus CBMAI 847 were selected for the reduction of 2-azido-1-phenylethanone derivatives 2–4. Whole cells of A. s
- Alvarenga, Natália,Porto, André L. M.
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p. 388 - 396
(2017/10/06)
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- Green click synthesis of β-hydroxy-1,2,3-triazoles in water in the presence of a Cu(ii)-azide catalyst: a new function for Cu(ii)-azide complexes
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A new Cu(ii)-azide complex, [Cu(H2L)(N3)]·CH3OH (1), was synthesized by the reaction of Cu(NO3)2 3H2O with 2-{[(1E)-(2-hydroxyphenyl)methylene]amino}-2-methylpropane-1,3-diol (H3
- Noshiranzadeh, Nader,Emami, Marzieh,Bikas, Rahman,Kozakiewicz, Anna
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p. 2658 - 2667
(2017/04/03)
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- Regioselective vicinal functionalization of unactivated alkenes with sulfonium iodate(i) reagents under metal-free conditions
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Metal-free, molecular iodine-free direct 1,2-difunctionalization of unactivated alkenes has been reported. The sulfonium iodate(i) reagent efficiently promoted the intermolecular vicinal iodo-functionalization of a diverse range of olefins in a stereo and regioselective manner. This method enables the divergent and straightforward preparation of synthetically useful functionalities; β-iodocarboxylates, β-iodohydrins, and β-iodoethers in a one-step process. Further interconversion of iodo-functionalized derivatives allows easy access to valuable synthetic intermediates en route to biologically active molecules.
- Rao, Dodla S.,Reddy, Thurpu R.,Babachary, Kalvacherla,Kashyap, Sudhir
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p. 7529 - 7543
(2016/08/16)
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- 2-Phenyl-2-(4-phenyl-1 H-1,2,3-triazol-1-yl)ethanol as an efficient and versatile auxiliary ligand in copper(II)-catalyzed Buchwald-Hartwig and Sharpless-Meldal C-N bond-forming reactions
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A highly active, air-stable, and versatile procedure for Buchwald-Hartwig and Sharpless-Meldal C-N bond formation is reported. Under nearly solvent-free conditions using copper(II) acetate and 2-phenyl-2-(4-phenyl-1H-1,2,3-triazol-1-yl)ethanol, a variety of N-heterocycles and various cyclic and noncyclic secondary amines were arylated to form N-aryl compounds in moderate to excellent yields. This methodology also provides rapid access to diverse 1,4-disubstituted 1,2,3-triazoles in good to excellent yields. All reactions are performed in short times under air.
- Sharghi, Hashem,Shiri, Pezhman
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p. 1131 - 1146
(2015/04/14)
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- Stereoselective radical azidooxygenation of alkenes
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Radical azidooxygenation of various alkenes is described. A readily prepared N3-iodine(III) reagent acts as a clean N3-radical precursor. Radical generation is achieved with TEMPONa acting as a mild organic reducing reagent. The C-radical generated after N3-radical addition is efficiently trapped by in situ generated TEMPO. Yields are good to excellent, and for cyclic systems azidooxygenation occurs with excellent diastereoselectivity.
- Zhang, Bo,Studer, Armido
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supporting information
p. 4548 - 4551
(2013/09/24)
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- Click chemistry inspired structural modification of azole antifungal agents to synthesize novel 'drug like' molecules
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A new class of 'drug like' 1,4-disubstituted-1,2,3-triazoles is synthesized using one-pot reaction of sodium azide, α-bromo ketones, and alkynes in PEG-400/water (1:1, v/v) under the click chemistry reaction condition followed by reduction of keto group and alkylation. The method is simple, efficient and gives good yield of novel 1,2,3-triazole derivatives.
- Pericherla, Kasiviswanadharaju,Khedar, Poonam,Khungar, Bharti,Kumar, Anil
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supporting information
p. 6761 - 6764
(2013/01/15)
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- Environmental friendly azide-alkyne cycloaddition reaction of azides, alkynes, and organic halides or epoxides in water: Efficient "click" synthesis of 1,2,3-triazole derivatives by Cu catalyst
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An efficient click synthesis of 1,2,3-triazole derivatives from benzyl halides or alkyl halides, epoxides, terminal alkynes, and sodium azides in the presence of copper salts and relative benzimidazole salts have been developed. This procedure eliminates the need to handle potentially organic azides, which are generated in situ. A broad spectrum of substrates can participate in the process effectively to produce the desired products in good yields.
- Liu, Jianming,Liu, Muwen,Yue, Yuanyuan,Yao, Meihuan,Zhuo, Kelei
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experimental part
p. 644 - 650
(2012/05/20)
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- Zeo-click chemistry: Copper(I)-zeolite-catalyzed cascade reaction; One-pot epoxide ring-opening and cycloaddition
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Copper(I)-modified zeolites, especially CuI-USY, proved to be very efficient catalysts in multi-component reactions of epoxides with sodium azide and terminal alkynes. Such catalysts allow highly regio- and stereoselective syntheses ofhydroxyme
- Boningari, Thirupathi,Olmos, Andrea,Reddy, Benjaram M.,Sommer, Jean,Pale, Patrick
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experimental part
p. 6338 - 6347
(2011/03/17)
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- Library of 1,4-disubstituted 1,2,3-triazole analogs of oxazolidinone RNA-binding agents
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The design and synthesis of small molecules that target RNA is immensely important in antibacterial therapy. We had previously reported on the RNA binding of a series of 4,5-disubstituted 2-oxazolidinones that bind to a highly conserved bulge region of bacterial RNA. This biological target T box antitermination system, which is found mainly in Gram-positive bacteria, regulates the expression of several amino acid related genes. In an effort to amplify our library, we have prepared a library of 1,4-disubstituted 1,2,3-triazole analogs that entails an isosteric replacement of the oxazolidinone nucleus. The synthesis of the new analogs was enhanced via copper(I) catalysis of an azide and alkyne cycloaddition reaction. A total of 108 1,4-disubstituted 1,2,3-triazole compounds have been prepared. All compounds were evaluated as RNA binding agents.
- Acquaah-Harrison, George,Zhou, Shu,Hines, Jennifer V.,Bergmeier, Stephen C.
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body text
p. 491 - 496
(2010/09/15)
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- One pot 'click' reactions: Tandem enantioselective biocatalytic epoxide ring opening and [3+2] azide alkyne cycloaddition
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Halohydrin dehalogenase (HheC) can perform enantioselective azidolysis of aromatic epoxides to 1,2-azido alcohols which are subsequently ligated to alkynes producing chiral hydroxy triazoles in a one-pot procedure with excellent enantiomeric excess. The Royal Society of Chemistry 2010.
- Campbell-Verduyn, Lachlan S.,Szymanski, Wiktor,Postema, Christiaan P.,Dierckx, Rudi A.,Elsinga, Philip H.,Janssen, Dick B.,Feringa, Ben L.
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supporting information; experimental part
p. 898 - 900
(2010/06/12)
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- One-pot, three-component synthesis of 1-(2-hydroxyethyl)-1H-1,2,3-triazole derivatives by copper-catalyzed 1,3-dipolar cycloaddition of 2-azido alcohols and terminal alkynes under mild conditions in water
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A safe, efficient, and improved procedure for the regioselective synthesis of 1-(2-hydroxyethyl)-1H-1,2,3-triazole derivatives under ambient conditions is described. Terminal alkynes reacted with oxiranes and NaN3 in the presence of a copper(I)
- Sharghi, Hashem,Hosseini-Sarvari, Mona,Moeini, Fatemeh,Khalifeh, Reza,Beni, Alireza Salimi
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experimental part
p. 435 - 449
(2010/05/19)
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- Immobilization of porphyrinatocopper nanoparticles onto activated multi-walled carbon nanotubes and a study of its catalytic activity as an efficient heterogeneous catalyst for a click approach to the three-component synthesis of 1,2,3-triazoles in water
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An efficient, regioselective, one-pot and two-step synthesis of β-hydroxy 1,4-disubstituted 1,2,3-triazoles from a wide range of non-activated terminal alkynes and epoxides and sodium azide by way of a three-component click reaction using a catalytic amount of [meso-tetrakis(o- chlorophenyl)porphyrinato]copper(II) (5 mol%) in excellent isolated yields is described. The reactions were performed in water as a green solvent at ambient temperature without any additives. By performing two reaction steps in one pot and purifying only at the final step, this procedure excludes any interim purification of in situ generated organic azide intermediates, which significantly improves the overall yield and reduces the reaction time. To benefit from the recovery and reuse of the catalyst, a new heterogeneous catalyst was prepared by simple and successful impregnation of the catalyst onto activated multi-walled carbon nanotubes (AMWCNT). The heterogeneous catalyst was characterized by powder X-ray diffraction (XRD), transmission electron microscopy (TEM), scanning electron microscopy (SEM), atomic forced microscopy (AFM), and thermogravimetric (TG) analysis to estimate the amount of nitrogen adsorption, and Raman and FT-IR spectroscopy. Leaching experiments after ten successive cycles showed that the catalyst is most strongly anchored to the AMWCNT support. Mechanistically, porphyrinatocopper catalyzes each step of the reaction in different ways as a bifunctional catalyst including epoxide ring opening by azide delivery to epoxide, forming in situ generated 2-azido alcohols followed by activation of the C≡C triple bond of the starting terminal alkynes by forming a porphyrinatocopper-acetylide intermediate and thereby promoting the [3+ 2]-cycloaddition reaction as the key step to form the triazole framework.
- Sharghi, Hashem,Beyzavi, Mohammad Hassan,Safavi, Afsaneh,Doroodmand, Mohammad Mahdi,Khalifeh, Reza
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experimental part
p. 2391 - 2410
(2009/12/29)
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