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1.
A series of 1,4-disubstituted 1,2,3-triazoles containing formyl was synthesized from a variety of readily available nitrobenzaldehydes and alkynes via a convenient one-pot, click-SNAr reaction with moderate to excellent yields. The reactions were easily carried out in hexamethyl phosphoramide in the absence of a base at 60 °C.  相似文献   

2.
1,2,3-三氮唑衍生物是近些年研究热点化合物之一,随着4-单取代型衍生物在医药、农药、材料等领域的广泛应用,该类化合物的合成及应用近些年引起了广大研究者的关注并获得了可喜进展。本文阐述了4-单取代-1,2,3-三氮唑衍生物的合成发展历史,着重综述了近十年来该类唑衍生物的合成发展情况。内容主要包括末端炔的环加成反应、由取代烯烃合成法及由3-芳基-2,3-二溴丙酸合成法。文章还包括一些合成方法及其产物的应用,并对一些重要的反应机理做了分析。文章最后对该类化合物的合成做了总结并展望了未来发展方向。  相似文献   

3.
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   

4.
A series of 1,5-disubstituted 1,2,3-triazoles are synthesized by a one-pot process from anti-3-aryl-2,3-dibromopropanoic acids and organic azides mediated by sodium hydride in dimethyl sulfoxide.The reaction is mild and simple,does not require a transition-metal catalyst,and gives products in good to excellent yields.  相似文献   

5.
Abstract

Polymer-supported copper-catalyzed one-pot synthesis of 1,4-disubstituted 1-alkyl- and 1-aryl-1,2,3-triazoles via 1,3-dipolar cycloaddition of alkyl halides or arylboronic acids, sodium azide, and phenylacetylene has been developed. Reactions went smoothly at room temperature using PEG/H2O or methanol as solvent to afford the corresponding triazoles in good to excellent yields. The catalyst could be recovered by simple filtration and reused several times with slightly decrease in its activity.  相似文献   

6.
The reaction of α-tosyloxy ketones, sodium azide, and terminal alkynes in presence of copper(I) in aqueous polyethylene glycol afforded regioselectively 1,4-disubstituted 1,2,3-triazoles in good yield at ambient temperature. The one-pot exclusive formation of 1,4-disubstituted 1,2,3-triazoles involves in situ formation of α-azido ketones, followed by cycloaddition reaction with terminal alkyne. The generality of this one-pot method was demonstrated by synthesizing an array of diverse 1,4-disubstituted 1,2,3-triazoles.  相似文献   

7.
A facile synthesis of 1,4-disubstituted 1,2,3-triazoles was achieved from nitrobenzenes and terminal alkynes under mild conditions. The reactions were successful for nitrobenzenes and terminal alkynes bearing various functionalities, from which the 1,2,3-triazole derivatives were smoothly synthesized through a four-step one-pot sequence.  相似文献   

8.
《Arabian Journal of Chemistry》2020,13(12):9047-9057
A Novel class of 1,4-disubstituted 1,2,3-triazoles have been synthesized in good to excellent yields via Cu(I) accelerated azide-alkyne click chemistry reaction strategy. The newly synthesized compounds were assessed for their in vitro antimicrobial activity against five Gram-positive, seven Gram-negative bacteria and three fungi. Most of the synthesized compounds displayed significant activity against the tested Gram-positive and Gram-negative bacteria. Molecular docking study revealed that all docked compounds are bound efficiently with the active site of Topoisomerase IV (4EMV) receptor with the observed the free energy of binding from −7.79 to −9.44 kcal/mol. Interestingly, compound 13a forms four hydrogen bonds and displayed high binding energy (−9.44 kcal/mol) with the Topoisomerase IV (4EMV) receptor which correlated with their in vitro antimicrobial assays.  相似文献   

9.
1,4-Disubstituted 1,2,3-triazoles were obtained by a high-yielding copper(I) catalyzed 1,3-dipolar cycloaddition reaction between in situ generated azides and terminal acetylenes. This one-pot, two-step procedure tolerates most functional groups and circumvents the problems associated with the isolation of potentially toxic and explosive organic azides.  相似文献   

10.
1,2,3-三氮唑衍生物是近些年研究热点化合物之一,随着4-单取代型衍生物在医药、农药、材料等领域的广泛应用,该类化合物的合成及应用近些年引起了广大研究者的关注并获得了可喜进展。本文阐述了4-单取代-1,2,3-三氮唑衍生物的合成发展历史,着重综述了近十年来该类唑衍生物的合成发展情况。内容主要涵盖二取代-1,2,3-三氮唑的去取代基反应,包括脱羧、脱苄基、脱羟(酰氧)基及脱取代乙基等反应。文章还包括一些合成方法及其产物的应用,并对一些重要的反应机理做了分析。文章最后对该类化合物的合成做了总结并展望了未来发展方向。  相似文献   

11.
An efficient and practical route to 5-alkynyl-1,2,3-triazoles has been developed via heterogeneous tandem CuAAC/alkynylation reaction of organic azides, alkynes and 1-bromoalkynes by using an L-proline-functionalized MCM-41-anchored copper(I) complex [L-Proline-MCM-41-CuCl] as catalyst under mild conditions. The reaction produces a wide variety of 5-alkynyl-1,2,3-triazoles in mostly good to excellent yields. The new immobilized copper(I) complex can be readily prepared from commercially available and inexpensive reagents and displays the same catalytic activity as CuCl. The L-Proline-MCM-41-CuCl catalyst is also easy to recover via a simple filtration process and can be reused at least seven times without apparent loss of activity.  相似文献   

12.
A library of twenty five 1,2,3-triazoles bridged with amine-amide functionalities have been synthesized from reaction of N-substituted(prop-2-yn-1-yl)amines (2a–2e), 2-bromo-N-arylacetamides (4a–4e) and sodium azide through copper(I)-catalyzed alkyne-azide cycloaddition. The synthesized compounds were characterized by using FTIR, 1H NMR, 13C NMR, and HRMS techniques. The structures of synthesized 5a (CCDC 1569245) and 5h (CCDC 1569249) were also confirmed by X-ray crystallography. Antifungal evaluation of newly synthesized triazoles was carried out against – Candida albicans and Aspergillus niger. Biological screening of synthesized 1,2,3-triazoles revealed moderate to good antifungal activity against tested strains.  相似文献   

13.
(E)-β-Arylvinyl bromides were stereoselectively prepared in high yields by microwave irradiation of the corresponding anti-3-aryl-2,3-dibromopropanoic acids in AcOH in the presence of AgOAc for 0.5-3.0 min.  相似文献   

14.
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   

15.
1,4-Disubstituted 1,2,3-triazoles are obtained in excellent yields via a three-component coupling of secondary alcohols, alkynes and trimethylsilyl azide (TMSN3). This one-pot reaction occurs through in situ generation of an azide from the alcohol and TMSN3, followed by 1,3-dipolar cycloaddition of the terminal alkyne to afford the corresponding disubstituted triazoles.  相似文献   

16.
A simple and efficient synthesis of 6-substituted 2-(4-aryl-1,2,3-triazol-1-yl)pyrimidines and 7-deazapurines from readily available 6-chloro-2-methylthiopyrimidine and 6-chloro-2-methylthio-7-deazapurine derivatives is described. The synthetic strategy is based on sequential reactions: substitution of 6-chlorine group with amines or (2-pyridyl)tributylstannane, oxidation of the obtained 6-substituted 2-methylthiopyrimidines, and 7-deazapurines to the corresponding 2-methylsulfonyl derivatives, their conversion to 2-azido derivatives and Cu(I)-catalyzed azide???alkyne cycloaddition reaction with arylethynes.  相似文献   

17.
Published data on methods for the synthesis of substituted 4(5)-nitro-1,2,3-triazoles and their properties are reviewed. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 3–25, January, 2008.  相似文献   

18.
Polystyrene-supported 2-azidoethyl phenyl selenide and 3-azidopropyl phenyl selenide reagents have been developed and applied to the traceless solid-phase organic synthesis of 1-vinyl- and 1-allyl-1,2,3-triazoles by CuI-mediated azide–alkyne cycloadditions and subsequent cleavage from the polymer support through oxidation–elimination reaction with 30% hydrogen peroxide. The advantages of this method include straightforward operation, good yield and purity of the products, and good stability and lack of odor for the reagents.  相似文献   

19.
The Letter reports a safe and reliable synthesis of aryl 1,2,3-triazoles from the corresponding anilines via intermediate aryl azides, using a continuous process. The method was applied to a variety of substrates with good to excellent yields, without the need to isolate the reactive and possibly unstable intermediates which were constantly kept at low concentration in the matrix environment.  相似文献   

20.
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   

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