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1.
Srivari Chandrasekhar Mallikanti SeenaiahAbhishek Kumar Chada Raji ReddySuman Kumar Mamidyala Chityal Ganesh KumarSridhar Balasubramanian 《Tetrahedron letters》2011,52(7):806-808
Synthesis of a series of [1,2,3] triazolo [5,1-c] [1,4]benzoxazepine derivatives have been accomplished by the intramolecular Cu(I)-catalyzed cycloaddition of azido-alkynes derived from salicylaldehyde. The biological profile of these heterocyclic structural scaffolds toward anti-bacterial as well as anti-fungal activity has also been illustrated. 相似文献
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Conjugated alternative donor–acceptor type pyrrol-pyridazyl-triazolyl-pyridine N-heterocyclic systems were synthesized via Cu(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddition reaction of pyrrol-pyridazylacetylene with azidopyridines. 相似文献
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Light can be used as an activator for the in situ generated copper(I)-catalyzed click reaction between azides and alkynes without adding reducing agents. The accumulation of sufficient concentration of copper(I) throughout the reaction can successfully be achieved by UV irradiation, in the presence of air. 相似文献
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Intramolecular click chemistry was utilized to effect synthesis of the benzofused, triazole ring systems. The trimethylsilyl group was found to impede the reaction progress, and therefore, conditions employing in situ removal of the TMS group coupled with microwave irradiation give the penultimate targets with good conversion. 相似文献
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An efficient method is described for the regioselective synthesis of 1,4-disubstituted 1,2,3-triazoles in high yields from a variety of Baylis-Hillman acetates and terminal alkynes with sodium azide using CuI as a catalyst, in either water or polyethylene glycol (PEG). This procedure is operationally simple and environmentally benign. Polyethylene glycol (PEG) serves as an efficient reusable solvent with higher efficiency. 相似文献
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Jory Lietard 《Tetrahedron letters》2007,48(50):8795-8798
A new bromohexyl phosphoramidite was synthesized and used for the introduction of an azide function at the 5′-end of oligonucleotides after a treatment on solid support with sodium azide and sodium iodide. The corresponding 5′-azido oligonucleotide could be further used for ‘Click’ conjugation with alkyne derivatives or by Staudinger ligation. 相似文献
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Srivari Chandrasekhar Chennamaneni Lohitha Rao Chada Raji Reddy 《Tetrahedron letters》2007,48(33):5869-5872
The Cu(I)-catalyzed cycloaddition of azido-alkynes (click reaction) of furanose sugar substrates provides a facile approach for the construction of macrocyclic molecules via an inter and/or intramolecular cycloaddition based on the functionality between alkyne and azide. 相似文献
10.
Daria V. Vorobyeva Tamara P. Vasilyeva Grigory T. Shchetnikov Gerd-V. Röschenthaler 《Journal of fluorine chemistry》2010,131(3):378-877
A convenient method for the preparation of α-CF3-α-aminophosphonates bearing alkynyl group at the α-carbon atom has been described. New alkynylphosphonates have been further utilized in the synthesis of functionalized triazole-containing α-CF3-α-aminophosphonates via copper-catalyzed (3+2)-cycloaddition to different organic azides. 相似文献
11.
Spruell JM Dichtel WR Heath JR Stoddart JF 《Chemistry (Weinheim an der Bergstrasse, Germany)》2008,14(14):4168-4177
A one-pot sequential Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC) strategy is presented for the synthesis of constitutionally unsymmetrical cyclobis(paraquat-p-phenylene)-based rotaxanes in good yields from simple starting materials. The methodology consists of performing multiple CuAAC reactions to stopper a pseudorotaxane in a stepwise manner, the order of which is controlled through silyl-protection and Ag(I)-catalyzed deprotection of a terminal alkyne. The methodology is highlighted by the synthesis of an amphiphilic branched [4]rotaxane. The methodology increases the ability to access ever more complicated mechanically interlocked compounds to serve in devices as sophisticated and functional molecular machinery. 相似文献
12.
SUTHIWANGCHAROEN Nisaraporn 《中国科学:化学(英文版)》2012,55(1):125-130
Borondipyrromethenes(BODIPY) are a class of fluorescent dyes whose fluorescence quantum yields are generally high and independent of the solvent.In this paper,we report the synthesis of a new type of BODIPY compound that carries an azido group on the 3-position of the pyrrole core.The azido group quenches the fluorescence of the dye due to its weak electron-donating effect.The fluorescence of the BODIPY dye can be switched on after reacting with alkynes via a Cu(Ⅰ) catalyzed azide-alkyne cycloaddition(CuAAC) reaction.We further demonstrate that this azido-BODIPY compound can be used in the cell imaging applications. 相似文献
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Herein described was a straightforward method for the highly regioselective synthesis of 5-trifluoromethyl-1,2,3-triazole nucleoside analogues, which featured the utilization of tert-butyldimethylsilyl (TBDMS) group as the directing group in the 1,3-dipolar cycloaddition reactions. 4-tert-Butyldimethylsilyl-5-trifluoromethyl-1,2,3-triazole nucleoside analogues were generated as the only cycloaddition products in moderate yields (15-79%) via the treatment of glycosyl azides with 3,3,3-trifluoro-1-tert-butyldimethylsilylpropyne 1 in toluene at 85 °C. Removal of TBS groups in these triazole cycloadducts with tetrabutylammonium fluoride (TBAF) smoothly afforded the various 5-trifluoromethyl-1,5-disubstituted 1,2,3-triazole nucleoside analogues in good yields (40-88%). 相似文献
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Romain Lucas Rachida Zerrouki Robert Granet Pierre Krausz Yves Champavier 《Tetrahedron》2008,64(23):5467-5471
Starting from 5′-O-tosylthymidine, sequential azidation and Cu-catalyzed [3+2] azide–alkyne 1,3-dipolar cycloaddition led to the formation of a 3′,5′-pentathymidine in high yield. The whole process needed only work-up/precipitation steps and was completed within just 18 min, thanks to microwave activation. 相似文献
15.
Changwei ShaoRui Zhu Sheng LuoQun Zhang Xinyan Wang Yuefei Hu 《Tetrahedron letters》2011,52(29):3782-3785
A simple combination of Cu2O and PhCO2H ‘on H2O’ has been developed as a highly practical and efficient catalytic system for copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC). It not only provides a further evidence for the strategy of carboxylic acids-promoted CuAAC, but also offers significant advantages to CuAAC because Cu2O is one of the most stable and cheapest Cu(I) sources; PhCO2H is one of the structurally simplest bidentate ligands; and water is the most ‘green’ solvent. 相似文献
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Xingqiang ChenGeorge N. Khairallah Richard A.J. O’HairSpencer J. Williams 《Tetrahedron letters》2011,52(21):2750-2753
High-resolution multistage mass spectrometric studies of isotope-labelled derivatives of a fixed-charge labelled sugar triazole assisted the identification of 5-hydroxy-1,2,3-triazoles as byproducts of the copper(I)-catalyzed cycloaddition of azides and terminal alkynes. Reaction optimization with inclusion of the auxiliary ligand, tris(benzyltriazolylmethyl)amine furnished an improved ligation protocol in which formation of the 5-hydroxytriazole is mitigated. 相似文献
17.
An efficient protocol for the one-pot preparation of alkyl 3-aryl-5-methylisoxazole-4-carboxylates from aryl aldehydes is described. This method is readily amenable to the large scale preparation of isoxazoles as well as the parallel synthesis of isoxazole libraries. 相似文献
18.
Jairo Quiroga Jaime GálvezAlfredo Pérez Angela ValenciaRodrigo Abonia Braulio Insuasty 《Tetrahedron letters》2011,52(42):5471-5473
Novel pyrazolylpyrrolopyrroles were prepared by the three-component reaction of pyrazole-4-carbaldehydes, α-amino acid esters and 1-arylmaleimides in toluene and in the absence of a catalyst. This protocol provided a simple one-step procedure for the synthesis of the title compounds with the advantage of an easy work-up, mild reaction conditions and endo-selectivity. 相似文献
19.
Wang Q Chan TR Hilgraf R Fokin VV Sharpless KB Finn MG 《Journal of the American Chemical Society》2003,125(11):3192-3193
The copper-catalyzed cycloaddition reaction between azides and alkynes functions efficiently in aqueous solution in the presence of a tris(triazolyl)amine ligand. The process has been employed to make rapid and reliable covalent connections to micromolar concentrations of protein decorated with either of the reactive moieties. The chelating ligand plays a crucial role in stabilizing the Cu(I) oxidation state and protecting the protein from Cu(triazole)-induced denaturation. Because the azide and alkyne groups themselves are unreactive with protein residues or other biomolecules, their ligation is of potential utility as a general bioconjugation method. 相似文献
20.
Loredana Maiuolo Beatrice Russo Vincenzo Algieri Monica Nardi Maria Luisa Di Gioia Matteo Antonio Tallarida Antonio De Nino 《Tetrahedron letters》2019,60(9):672-674
A simple procedure to obtain 1,5-disubstituted 1,2,3-triazoles, using the Er(OTf)3/[mpy]OTf/H2O catalytic system is described. The reaction proceeds through an eliminative azide–olefin cycloaddition (EAOC) offering a highly regioselective approach and good yields (81–94%). The advantages of this method include simple operations of work-up and the ability of the catalytic system to be re-used five times without an evident loss in yield. The role of IL and water were speculated, invoking also a probable ionic self-assembly (ISA) effect. 相似文献