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1.
In this three-component reaction, alkynes undergo a copper(I)-catalyzed cycloaddition with sodium azide and formaldehyde to yield 2-hydroxymethyl-2 H-1,2,3-triazoles, which are useful intermediates that can be readily converted to polyfunctional molecules. The hydroxymethyl group can also be removed, providing convenient access to N H-1,2,3-triazoles. The reaction is experimentally simple and readily scalable. 相似文献
2.
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
3.
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
4.
Yan W Wang Q Lin Q Li M Petersen JL Shi X 《Chemistry (Weinheim an der Bergstrasse, Germany)》2011,17(18):5011-5018
The N-2-aryl-1,2,3-triazole derivatives (NATs) were developed as a new class of UV/blue-light-emitting fluorophores. Though both N-1-aryl-1,2,3-triazoles and N-2-aryl-1,2,3-triazoles gave strong photo absorption under excitation at 330 nm, only the N-2-analogous showed strong fluorescence emission in the UV/blue range with high efficiency in various solvents (quantum yield Φ around 0.3-0.5). Significant substituted group effects were observed, allowing tunable optical properties with emission (λ(max)) from 350-400 nm and Stokes shift from 38-93 nm. The computational studies along with X-ray crystal structures indicated the significance of the effective conjugation between triazole ring and aryl groups on the N-2 position. The planar intramolecular charge transfer (PICT) mechanism was proposed, which was supported by solvent effect studies. Simple derivatizations gave NAT-modified lysine and strong UV/blue emitting bis-NAT (Φ=0.76, λ(max)=390), which suggested the great potential of this new class of fluorophores in biological and material science research. 相似文献
5.
An effective strategy for the synthesis of N-2-substituted-1,2,3-triazoles with excellent yields and regioselectivity has been developed. 相似文献
6.
Reaction of O-acyl-protected glycosylthiols with dichloromethane afforded readily glycosylthiomethyl chlorides, which gave with sodium azide the corresponding glycosylthiomethyl azides 17-22. Reaction of these azides with dicyclopentadiene as dipolarophile led to tandem 1,3-dipolar cycloaddition/retro-Diels-Alder reaction furnishing the parent 1-glycosylthiomethyl-1,2,3-triazoles 23-25. Reaction of azides with acetylene derivatives gave directly 1-glycosylthiomethyl-1,2,3-triazoles which are ring-substituted. 相似文献
7.
A. T. Baryshnikov V. I. Erashko N. I. Zubanova B. I. Ugrak S. A. Shevelev A. A. Fainzil'berg A. L. Laikhter L. G. Mel'nikova V. V. Semenov 《Russian Chemical Bulletin》1992,41(4):751-757
Several chemoselective syntheses have been developed for 4-nitro-1,2,3-triazoles from sodium azide and gem-dinitroethylenes prepared from readily available transformation products of dinitroacetic acid ester: N-(,-dinitroethyl)-N,N-dialkylamines, 2,2-dinitroethanol acetate, a mixture of dinitroacetic acid ester with aliphatic aldehydes, or 1,1,1-trinitroalkanes. Hitherto-unknown 4-nitro-5-amino- and 4,5-dinitro-1,2,3-triazoles have been synthesized via successive transformations of the CH3 groups in 5-nitro-4-methyltriazole. Nitration of 4-nitro-1,2,3-triazole with nitronium fluoroborate or acetyl nitrate gave an unknown 2,4-dinitro-1,2,3-triazole.N. D. Zelinskii Institute of Organic Chemistry, Russian Academy of Sciences, Moscow 117913. Translated from Izvestiya Akademii Nauk, Seriya Khimicheskaya, No. 4, pp. 958–966, April, 1992. 相似文献
8.
Synthetically useful rhodium(II) carbenes were obtained from N-(1,2,4-triazolyl)-substituted 1,2,3-triazoles and Rh(II) carboxylates. The electron-withdrawing 1,2,4-triazolyl group reveals the heretofore unknown reactivity of nonsulfonyl 1,2,3-triazoles, which exhibit the reactivity of diazo compounds. The resulting carbenes provide ready asymmetric access to secondary homoaminocyclopropanes (80-95% ee, dr >20:1) via reactions with olefins and also engage in efficient transannulation reactions with nitriles. 相似文献
9.
A one-pot method for the synthesis of 4,5-disubstituted-1,2,3-(NH)-triazoles via carbonylative Sonogashira reaction/1,3-dipolar cycloaddition of terminal acetylenes, carbon monoxide, aryl iodides, and sodium azide was developed. A series of new 4,5-disubstituted-1,2,3-(NH)-triazoles were prepared readily under mild conditions. 相似文献
10.
The CH acidity of all possible N-methyl substituted nitrotriazoles as well as of some 4-substituted 1,2,3-triazoles and N-alkyl-4-nitro-1,2,3-triazoles in the gas phase and in THF and DMSO solution has been calculated with the density functional theory B3LYP method. Electronic effects of substituents on the CH acidity of 4-substituted 1,2,3-triazoles have been examined using linear free energy relationship (LFER) methodology. In order to investigate the relation between the CH acidity of the heterocycles and their ability to undergo electrophilic substitution involving C-H bond cleavage, we have studied the reaction of isomeric N-alkyl-4-nitro-1,2,3-triazoles (alkyl=methyl, ethyl, isopropyl and tert-butyl) with HgBr2 in alkali solution. It was found that 1-isomers undergo mercuration readily, while mercuration of 2-substituted compounds do not occur under the same conditions, which is in agreement with the results of DFT calculations of the CH acidity of the compounds, showing that 2-isomers have considerably lower CH acidity than 1-isomers. 相似文献
11.
V. I. Boev V. N. Kushnir M. I. Shevchuk A. V. Dombrovskii 《Chemistry of Heterocyclic Compounds》1980,16(5):550-552
Ferrocenesulfonyl azide reacts with a number of aroylmethylenetriphenylphosphinomethylenes in dry methylene chloride to give 1,4,5-trisubstituted 1,2,3-triazoles (61–77% yields), which are readily converted to 4,5-disubstituted 1,2,3-triazoles and ethyl ferrocenesulfonate when they are refluxed in ethanol. The known tri-phenylphosphazo ferrocenyl sulfone and ethyl diazoacetate are formed in the case of the reaction of ferrocenesulfonyl azide with carbethoxymethylenetriphenylphosphinomethylene. The structures of the synthesized compounds were proved by the results of elementary analysis and IR, UV, and mass spectroscopy.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 701–704, May, 1980. 相似文献
12.
[reaction: see text] 1,4-Disubstituted 1,2,3-triazoles are obtained in excellent yields by a convenient one-pot procedure from a variety of readily available aromatic and aliphatic halides without isolation of potentially unstable organic azide intermediates. 相似文献
13.
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
14.
15.
Sulfamoyl azides are readily generated from secondary amines and a novel sulfonyl azide transfer agent, 2,3-dimethyl-1H-imidazolium triflate. They react with alkynes in the presence of a CuTC catalyst forming 1-sulfamoyl-1,2,3-triazoles. The latter are shelf-stable progenitors of rhodium azavinyl carbenes, versatile reactive intermediates that, among other reactions, readily and asymmetrically add to olefins. 相似文献
16.
An efficient and economic system for the synthesis of N-2-aryl-substituted 1,2,3-triazoles in the presence of CuFe2O4 was developed. The corresponding products can be obtained in good to excellent yields. It is interesting to note that the catalyst could be reused for five consecutive trials without significant decreases in its activity. 相似文献
17.
The interesting bioactivities of 2(5H)-furanone, 1,2,3-triazole, and amino acid derivatives have promoted their combination into one multifunctional molecule. The symmetrical bis-1,2,3-triazoles and mono-1,2,3-triazoles with one free azide group are synthesized respectively by controlling the molar ratio of reactants, N-[5-alkoxy-2(5H)-furanonyl] amino acid propargyl ester and 1,4-diazidobutane. The unsymmetrical bis-1,2,3-triazoles are afforded by the subsequent reaction of mono-1,2,3-triazoles with other terminal alkynes with good to excellent yields in a short time under the same mild “click” reaction conditions. The 32 new compounds obtained in the reactions are characterized by Fourier transform infrared, 1H NMR, 13C NMR, mass spectrometry, and elemental analysis. Because of the diversity of four or five basic units in molecule, this methodology provides easy access to different chiral 2(5H)-furanone compounds with polyheterocyclic structure, especially with unsymmetrical bis-1,2,3-triazole moiety. Importantly, a simple approach is provided for the synthesis of unsymmetrical bis-1,2,3-triazoles using common diazides. 相似文献
18.
Mariola Koszytkowska-Stawińska Ewa Mironiuk-Puchalska Tomasz Rowicki 《Tetrahedron》2012,68(1):214-225
2-Substituted-2H-1,2,3-triazolo-nucleosides with 3-phosphonopropyl, 2-hydroxyethyl, 2-cyanoethyl, carbamoylmethyl, or 1-deoxy-2,5-anhydro-d-mannitol-1-yl on the triazole N-2 nitrogen atom were obtained via the DBU-promoted N-alkylation of 3-(pivaloyloxymethyl)-1-[(NH-1,2,3-triazol-4-yl)methyl]thymine with diethyl 3-bromopropylphoshonate, 2-bromoethanol, acrylonitrile, methyl bromoacetate, or 3,4,6-tris(O-benzoyl)-2,5-anhydro-d-mannitol 1-tosylate. The N-2/N-1 regioselectivity of the alkylation varied from 57/43 (methyl bromoacetate) to 97/3 (diethyl 3-bromopropylphoshonate). The 1-substituted-1H-1,2,3-triazoles, when formed in the appreciated amount in the alkylation reaction, were converted into the corresponding 1-substituted-1H-1,2,3-triazolo-nucleosides. The substitution pattern of 2-substituted-2H-1,2,3-triazolo-nucleosides was confirmed by 1H–15N HMBC NMR spectra; the triazole nitrogen atoms were identified through their correlations with the triazole exo-cyclic protons. 相似文献
19.
Raju Jannapu Reddy Angothu Shankar Md. Waheed Jagadeesh Babu Nanubolu 《Tetrahedron letters》2018,59(21):2014-2017
A convenient and metal-free protocol for the highly regioselective sulfonylation of NH-1,2,3-triazoles is described. A range of readily accessible NH-1,2,3-triazoles were sulfonylated with various aryl sulfinates in the presence of molecular iodine. The scope was extended to thiosulfonates as an efficient sulfonylating agent and nitrochromene derived triazoles were also explored for selective N-sulfonylation. A variety of synthetically viable N2-sulfonyl triazoles were obtained in moderate to high yields with excellent regioselectivities via N–S bond construction under mild reaction conditions. 相似文献
20.
Chuprakov S Malik JA Zibinsky M Fokin VV 《Journal of the American Chemical Society》2011,133(27):10352-10355
A highly efficient enantioselective C-H insertion of azavinyl carbenes into unactivated alkanes has been developed. These transition metal carbenes are directly generated from readily available and stable 1-sulfonyl-1,2,3-triazoles in the presence of chiral Rh(II) carboxylates and are used for C-H functionalization of alkanes to access a variety of β-chiral sulfonamides. 相似文献