共查询到20条相似文献,搜索用时 31 毫秒
1.
Jiamei Wei Jie Chen Jiechao Xu Long Cao Hongmei Deng Weihua Sheng Hui Zhang Weiguo Cao 《Journal of fluorine chemistry》2012
1,3-Dipolar cycloadditions of methyl 2-perfluoroalkynoates with various azides have been examined, leading to a simple metal-free synthetic protocol for the synthesis of perfluoroalkylated 1,2,3-triazoles. The regiochemical results demonstrated that the cycloaddition was controlled by FMO (the frontier molecular obitals) interaction and steric hindrance in transition states. 相似文献
2.
A metal-free and solvent free click-chemistry procedure has been revealed for the synthesis of 4-trifluoroacetyl-1,2,3-triazoles from corresponding azides and alkyne with high yield and selectivity. The pure products could be easily obtained via crystallization of the reaction mixture (standing for 1 day). Among the 4-trifluoroacetyl-1,2,3-triazoles, 3ba showed the best anticancer activity against HepG2 cell with IC50 of 0.0267?μmol/ml. This method has the advantages of less pollution, low cost, simple treatment and more efficiency. 相似文献
3.
Marie-Claire Giel Dr. Christopher J. Smedley Emily R. R. Mackie Taijie Guo Prof. Dr. Jiajia Dong Dr. Tatiana P. Soares da Costa Prof. Dr. John E. Moses 《Angewandte Chemie (Weinheim an der Bergstrasse, Germany)》2020,132(3):1197-1202
The boom in growth of 1,4-disubstituted triazole products, in particular, since the early 2000’s, can be largely attributed to the birth of click chemistry and the discovery of the CuI-catalyzed azide–alkyne cycloaddition (CuAAC). Yet the synthesis of relatively simple, albeit important, 1-substituted-1,2,3-triazoles has been surprisingly more challenging. Reported here is a straightforward and scalable click-inspired protocol for the synthesis of 1-substituted-1,2,3-triazoles from organic azides and the bench stable acetylene surrogate ethenesulfonyl fluoride (ESF). The new transformation tolerates a wide selection of substrates and proceeds smoothly under metal-free conditions to give the products in excellent yield. Under controlled acidic conditions, the 1-substituted-1,2,3-triazole products undergo a Michael addition reaction with a second equivalent of ESF to give the unprecedented 1-substituted triazolium sulfonyl fluoride salts. 相似文献
4.
Harju K Vahermo M Mutikainen I Yli-Kauhaluoma J 《Journal of combinatorial chemistry》2003,5(6):826-833
The solid-phase synthesis of 1,2,3-triazoles via 1,3-dipolar cycloaddition of polymer-bound azides to various alkynes is reported. Polymer-bound azides were synthesized from polymer-bound halides and sodium azide and reacted with alkynes to produce polymer-bound 1,2,3-triazoles. Cleavage of the triazoles was performed with trifluoroacetic acid. A traceless synthesis of 1,2,3-triazoles was developed using 2-methoxy-substituted resin (polymer-bound 4-hydroxy-2-methoxybenzyl alcohol). In addition, a synthesis of 4-hydroxybenzyl-substituted 1,2,3-triazoles from the bromo-Wang resin (4-(bromomethyl)phenoxymethyl polystyrene) was achieved. 相似文献
5.
The first example of autocatalytic hydrolyzation of 4-aryl-1-tosyl-1,2,3-triazoles induced by p-toluenesulfonic acid was reported, providing an effective and metal-free synthetic approach to deliver a broad range of new 4-aryl-2H-1,2,3-triazoles in good yields. The kinetic profile of this hydrolyzation suggested that this reaction has exponential autocatalytic behavior. 相似文献
6.
Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(i)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides 总被引:1,自引:0,他引:1
The cycloaddition of azides to alkynes is one of the most important synthetic routes to 1H-[1,2,3]-triazoles. Here a novel regiospecific copper(I)-catalyzed 1,3-dipolar cycloaddition of terminal alkynes to azides on solid-phase is reported. Primary, secondary, and tertiary alkyl azides, aryl azides, and an azido sugar were used successfully in the copper(I)-catalyzed cycloaddition producing diversely 1,4-substituted [1,2,3]-triazoles in peptide backbones or side chains. The reaction conditions were fully compatible with solid-phase peptide synthesis on polar supports. The copper(I) catalysis is mild and efficient (>95% conversion and purity in most cases) and furthermore, the X-ray structure of 2-azido-2-methylpropanoic acid has been solved, to yield structural information on the 1,3-dipoles entering the reaction. Novel Fmoc-protected amino azides derived from Fmoc-amino alcohols were prepared by the Mitsunobu reaction. 相似文献
7.
Vito Fiandanese Daniela Bottalico Giuseppe Marchese Angela Punzi Francesca Capuzzolo 《Tetrahedron》2009,65(51):10573-1195
A convenient synthesis of 4-alkynyl-1,2,3-triazoles and novel unsymmetrically substituted 4,4′-bi-1,2,3-triazole derivatives has been devised starting from easily available 1-trimethylsilyl-1,3-butadiyne. The starting compound was reacted with several azides, leading to 4-(silylalkynyl)-1,2,3-triazoles, which were easily transformed into 4-arylalkynyl-1,2,3-triazoles by a Pd catalyzed coupling reaction with aryl halides, or into novel 4,4′-bi-1,2,3-triazole derivatives by a subsequent cyclization reaction with azides. 相似文献
8.
《Tetrahedron letters》2014,55(51):7026-7028
An environmentally friendly and efficient method for synthesis of 1,4-disubstituted 5-iodo-1,2,3-triazoles through [Cu(phen)(PPh3)2]NO3-catalyzed cycloaddition of organic azides and iodoalkynes under solvent-free conditions was developed. Based on this, a one-pot method for the synthesis of fully substituted 1,2,3-triazoles via cycloaddition/Suzuki reactions was also demonstrated in this report. 相似文献
9.
In this paper, an efficient synthesis of 5-alkynyl-1,2,3-triazoles through a one-pot aerobic oxidative coupling reaction of various alkynes and azides has been developed. Further derivatization of 5-alkynyl-1,2,3-triazoles readily yielded 5-carbonyl-1,2,3-triazoles, 5-carboxylic-1,2,3-triazole, 5-hydroxyalkyl-1,2,3-triazoles and 5-quinoxaline-1,2,3-triazole, which provided an entry into structurally diverse 5-functionalized-1,2,3-triazoles. 相似文献
10.
In this study, a new methodology for the one-pot synthesis of 4-aryl-1H-1,2,3-triazoles from arylglyoxaldoxime semicarbazone is presented. 4-Aryl-1,2,3-triazoles were obtained in moderate to good yields via sodium dithionite and O2, which are all efficient, safe and inexpensive reagents. This reaction is more suitable for large-scale syntheses than those using hydrazoic acid, sodium azide, or organic azides. 相似文献
11.
In this paper, an efficient synthesis of 5-alkynyl-1,2,3-triazoles through a one-pot aerobic oxidative coupling reaction of various alkynes and azides has been developed. Further derivatization of 5-alkynyl-1,2,3-triazoles readily yielded 5-carbonyl-1,2,3-triazoles, 5-carboxylic-1,2,3-triazole, 5-hydroxyalkyl-1,2,3-triazoles and 5-quinoxaline-1,2,3-triazole, which provided an entry into structurally diverse 5-functionalized-1,2,3-triazoles. 相似文献
12.
Sanders BC Friscourt F Ledin PA Mbua NE Arumugam S Guo J Boltje TJ Popik VV Boons GJ 《Journal of the American Chemical Society》2011,133(4):949-957
Although metal-free cycloadditions of cyclooctynes and azides to give stable 1,2,3-triazoles have found wide utility in chemical biology and material sciences, there is an urgent need for faster and more versatile bioorthogonal reactions. We have found that nitrile oxides and diazocarbonyl derivatives undergo facile 1,3-dipolar cycloadditions with cyclooctynes. Cycloadditions with diazocarbonyl derivatives exhibited similar kinetics as compared to azides, whereas the reaction rates of cycloadditions with nitrile oxides were much faster. Nitrile oxides could conveniently be prepared by direct oxidation of the corresponding oximes with BAIB, and these conditions made it possible to perform oxime formation, oxidation, and cycloaddition as a one-pot procedure. The methodology was employed to functionalize the anomeric center of carbohydrates with various tags. Furthermore, oximes and azides provide an orthogonal pair of functional groups for sequential metal-free click reactions, and this feature makes it possible to multifunctionalize biomolecules and materials by a simple synthetic procedure that does not require toxic metal catalysts. 相似文献
13.
P. Surendra Reddy 《Tetrahedron letters》2010,51(31):4037-1585
This protocol is for an expedient and operationally simple synthesis of allylic azides and one-pot synthesis of 1,4-disubstituted 1,2,3-triazoles from homoallyl alcohols. Synthesis of allylic azides involves the palladium-catalyzed hydroazidation of unactivated olefins with migration of double bond. This hydroazidation can be coupled to Cu(I) promoted 1,3-dipolar cycloaddition to afford the corresponding 1,4-disubstituted 1,2,3-triazoles. 相似文献
14.
After revisiting earlier works reporting the regioselective synthesis of 1,5-disubstituted-1,2,3-triazoles via the addition of bromomagnesium acetylides to azides, much improved yields of the products were obtained for a wide array of azides and alkynes. The intermediates of that reaction can be trapped with different electrophiles to regioselectively form 1,4,5-trisubstituted 1,2,3-triazoles. [reaction: see text] 相似文献
15.
Ian F. Cottrell David Hands Peter G. Houghton Guy R. Humphrey Stanley H. B. Wright 《Journal of heterocyclic chemistry》1991,28(2):301-304
A procedure for the preparation of substituted 1-benzyl-1H-1,2,3-triazoles from benzyl azides under very mild conditions is described. The method provides improved yields and extends the scope of the Dimroth Reaction to other types of active methylene compound to those previously used. Benzyl azides react with active methylene compounds in dimethyl sulphoxide catalysed by potassium carbonate at 35–40° to give 1H-1,2,3-triazoles usually in good yield. Acetonitrile derivatives gave 5-amino-1H-1,2,3-triazoles whereas diethyl malonate gave 5-hydroxy-1H-1,2,3-triazoles. 1H-1,2,3-Triazole-4-carboxylate esters and 1H-1,2,3-triazole-4-ketones were obtained from ethyl acetoacetate and β-diketones respectively. Benzyl methyl ketone reacted to give a 5-methyl-4-phenyl-1H-1,2,3-triazole, but acetone and acetophenone failed to react. Other active methylene compounds which did not react under these reaction conditions included ethyl cyanoacetate, ethyl fluoroacetate and ethyl nitroacetate. 相似文献
16.
Polystyrene-supported but-3-ynyl sulfonate reagent has been developed and applied to the traceless solid-phase organic synthesis of 1-substituted-4-vinyl-1,2,3-triazoles by CuI-promoted 1,3-dipolar cycloaddition reaction with various organic azides and subsequent cleavage from the polymer support through elimination reaction mediated by 1.8-diazabicyclo[5,4,0]undec-7-ene (DBU). The advantages of this new synthetic method include simple operation and moderate to good yields of the products, as well as good stability of the reagent. 相似文献
17.
Yury A. Rozin Johann Leban Wim Dehaen Valentine G. Nenajdenko Vasiliy M. Muzalevskiy Oleg S. Eltsov Vasiliy A. Bakulev 《Tetrahedron》2012,68(2):614-618
1-Trifluoromethyl-substituted 1,3-dicarbonyl compounds are shown to undergo 100% regioselective cyclization in reactions with alkyl and aryl azides to form 4-acyl-5-trifluoromethyl-1,2,3-triazoles. The reaction represents a general method for the synthesis of otherwise difficulty available 4-acyl-5-trifluoromethyl-1,2,3-triazoles. The directing role of the trifluoromethyl group is discussed in the light of stepwise and concerted mechanisms for this reaction. 相似文献
18.
Pokhodylo N. T. Tupychak M. A. Obushak M. D. 《Russian Journal of Organic Chemistry》2022,58(2):209-218
Russian Journal of Organic Chemistry - The main synthetic approaches to 1,5-disubstituted 1,2,3-triazoles are considered. It is shown that the cycloaddition of aryl azides to phosphorus ketoylides... 相似文献
19.
20.
An efficient copper-free synthesis of 1-monosubstituted aryl 1,2,3-triazoles from sodium acetylide and aryl azides was developed, which was found suitable for various aryl azides and completed within 15 min at room temperature with moderate to excellent yields. 相似文献