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1.
4‐Aryl‐3,5‐bis(arylethynyl)aryl‐4H‐1,2,4‐triazoles: Multitasking Skeleton as a Self‐Assembling Unit
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M. Jesús Pastor Iván Torres Dr. Cristina Cebrián Dr. José Ramón Carrillo Dr. Ángel Díaz‐Ortiz Dr. Emilio Matesanz Julia Buendía Dr. Fátima García Dr. Joaquín Barberá Dr. Pilar Prieto Dr. Luis Sánchez 《Chemistry (Weinheim an der Bergstrasse, Germany)》2015,21(4):1795-1802
The synthesis of a series of 4‐aryl‐3,5‐bis(arylethynyl)aryl‐4H‐1,2,4‐triazoles derivatives is reported and the influence exerted by peripheral substitution on the morphology of the aggregates generated from these 1,2,4‐triazoles is investigated by SEM imaging. The presence of paraffinic side chains results in long fibrillar supramolecular structures, but unsubstituted triazoles self‐assemble into thinner ribbons and needle‐like aggregates. The crystals obtained from methoxy‐substituted triazoles have been utilised to elaborate a model that helps to justify aggregation of the investigated 1,2,4‐triazoles, in which the operation of arrays of C?H???π non‐covalent interactions plays a significant role. The results presented herein demonstrate the ability of simple molecules to behave as multitasking scaffolds with different properties, depending on peripheral substitution. Thus, although 1,2,4‐triazoles without long paraffinic side chains exhibit optical waveguiding behaviour, triazoles endowed with peripheral paraffinic side chains exhibit hexagonal columnar mesomorphism. 相似文献
2.
Michael Lartey Martijn Gillissen Brian J. Adzima Kenichi Takizawa David R. Luebke Hunaid B. Nulwala 《Journal of polymer science. Part A, Polymer chemistry》2013,51(16):3359-3364
The free radical reactivity ratios between styrene and different vinyl‐1,2,3‐triazole regioisomeric monomers in 1,4‐dioxane at 65 °C have been established using nonlinear least square method. The results obtained for the reactivity ratio between regioisomers show exceptionally different polymerization behavior, highlighting the effects of the electronic and steric factors of these regioisomeric monomers. The experimental results highlight the effects of the electronic and sterics on the copolymerization behavior. In case of 1,4‐vinyl‐triazoles, it was found that without the steric effects, the reactivity is very similar to that of styrene and forms random copolymers. However, it was found that 1,5‐vinyl‐triazoles are more reactive than 1,4‐vinyl triazoles. In the case of styrene‐co‐1,4‐vinyl‐1,2,3‐triazoles, the reactivity ratios were calculated to be rstyrene: r1‐octyl‐4‐vinyl‐triazole = 1.97:0.54, rstyrene : r1‐benzyl‐4‐vinyl‐triazole = 1.62:0.50, and rstyrene: r1‐methyl‐4‐vinyl‐triazole = 0.90:0.87. On the other hand, reactivity ratios for styrene‐co‐1,5‐vinyl‐1,2,3‐triazoles were found to be rstyrene: r1‐octyl‐5‐vinyl‐triazole = 0.13:0.66 and rstyrene: r1‐benzyl‐5‐vinyl‐triazole = 0.34:0.49. © 2013 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2013 , 51, 3359–3364 相似文献
3.
Treatment of 1,4‐disubstituted 1,2,3‐triazoles with aryl chlorides in the presence of potassium carbonate under palladium catalysis and microwave irradiation at 250 °C for 15 min leads to arylation of the triazole at the 5‐position. A variety of functional groups, including ester and hydroxy groups, are compatible. The procedure is suitable for the regioselective preparation of trisubstituted triazoles. Microwave irradiation accelerates the reaction, thus allowing the rapid synthesis of trisubstituted triazoles, which are difficult to synthesize selectively. 相似文献
4.
《应用有机金属化学》2017,31(10)
A new nanocatalyst was synthesized by immobilization of 4′‐(4‐hydroxyphenyl)‐2,2′:6′,2″‐terpyridine/CuI complex on ferromagnetic nanoparticles through a surface modification (FMNPs@SiO2‐TPy‐Cu). This heterogeneous catalyst was characterized using various techniques including Fourier transform infrared and energy‐dispersive X‐ray spectroscopies, transmission and scanning electron microscopies, X‐ray diffraction, vibrating sample magnetometry and thermogravimetric analysis. The resulting nanocatalyst presented excellent catalytic activity for the regioselective syntheses of 1,4‐disubstituted 1,2,3‐triazoles and thioethers. The thermally and chemically stable, benign and economical catalyst was easily recovered using an external magnet and reused in at least five successive runs without an appreciable loss of activity. 相似文献
5.
A highly efficient method for the synthesis of unsymmetrical multi‐substituted 1,2,3‐triazoles via a direct Pd‐NHC system catalyzed C(5)‐arylation of 1,4‐disubstituted triazoles, which are readily accessible via "click" chemistry has been developed. It is important to note that C? H bond functionalizations of 1,2,3‐triazoles with a variety of differently substituted aryl iodides and bromides as electrophiles can be conveniently achieved through this catalytic system at significantly milder reaction temperatures of 100°C under air. 相似文献
6.
Maryam Ciyabi Hashjin Roghayeh Ciyabi Maryam Baharloui Ghaffar Hosseini Hamed Tavakoli 《中国化学》2012,30(2):223-227
In this work, readily prepared copper supported on the SiO2 nanoparticles has been found to effectively catalyze the 1,3‐dipolar cycloaddition of a variety of azides, alkynes, epoxides and sodium azide, furnishing the corresponding 1,2,3‐triazoles and β‐hydroxytriazoles. Click reaction proceeds in short reaction times and under mild reaction conditions, and the resulting products are obtained in good yields at ambient temperature. 相似文献
7.
Abid H. Banday Bhupinder S. Arora Mohammed S. Alam Halmuthur M. Sampath Kumar 《Helvetica chimica acta》2007,90(12):2368-2374
Aryl azides 1 were treated with allenylmagnesium bromide ( 2 ) to generate 1,5‐disubstituted butynyl‐1H‐1,2,3‐triazoles 3 in a domino fashion, which upon CuI‐catalyzed 1,3‐dipolar cycloaddition with aryl azides 4 afforded novel bis‐1H‐1,2,3‐triazoles 5 in quantitative yields (Scheme 1 and Table). 相似文献
8.
A Metal‐Free Three‐Component Reaction for the Regioselective Synthesis of 1,4,5‐Trisubstituted 1,2,3‐Triazoles
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Dr. Joice Thomas Dr. Jubi John Nikita Parekh Prof. Dr. Wim Dehaen 《Angewandte Chemie (International ed. in English)》2014,53(38):10155-10159
A metal‐free three‐component reaction to synthesize 1,4,5‐trisubstituted 1,2,3‐triazoles from readily available building blocks, such as aldehydes, nitroalkanes, and organic azides, is described. The process is enabled by an organocatalyzed Knoevenagel condensation of the formyl group with the nitro compound, which is followed by the 1,3‐dipolar cycloaddition of the azide to the activated alkene. The reaction features an excellent substrate scope, and the products are obtained with high yield and regioselectivity. This method can be utilized for the synthesis of fused triazole heterocycles and materials with several triazole moieties. 相似文献
9.
Benedict's solution/ vitamin C: An alternative catalytic protocol for the synthesis of regioselective‐1,4‐disubstituted‐1H‐1,2,3‐triazoles at room temperature
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Manashjyoti Konwar Roktopol Hazarika Abdul A. Ali Mitali Chetia Nageshwar D. Khupse Prakash J. Saikia Diganta Sarma 《应用有机金属化学》2018,32(8)
A novel and highly efficient method for the synthesis of 1,4‐disubstituted‐1H‐1,2,3‐triazoles by copper‐catalyzed azide‐alkyne cycloaddition has been developed. This economic and sustainable protocol uses a readily available Benedict's solution/Vitamin C catalyst system affording a wide range of 1,4‐disubstituted‐1H‐1,2,3‐triazoles under mild conditions. 相似文献
10.
The condensation of 4‐amino‐3‐aryl‐5‐mercapto‐1, 2, 4‐triazoles (1a‐f) with 6‐/8‐substituted 1,4‐dihydro‐4‐oxo‐quinoline‐3‐carboxylic adds (2a‐d) in the presence of phosphorus oxychloride on refluxng or under microwave irradiation gave twenty four novel 3‐aryl‐6‐ (6‐/8‐substituted 4‐chloroquinoline‐3‐yl)‐s‐triazolo[3,4‐b]‐1, 3,4‐thiadiazoles (4a‐x), Considerable increase in the reaction rate has been observed with improved yields under microwave irradiation. The structures of the compounds synthesized were determined by elemental analyses, IR, 1H NMR and MS spectra. Their spectral properties and the reaction mechanism were also discussed. The preliminary biological test showed that some of compounds bad moderate antibacterial activities. 相似文献
11.
Metal‐Free Route for the Synthesis of 4‐Acyl‐1,2,3‐Triazoles from Readily Available Building Blocks
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Dr. Joice Thomas Vince Goyvaerts Prof. Dr. Sandra Liekens Prof. Dr. Wim Dehaen 《Chemistry (Weinheim an der Bergstrasse, Germany)》2016,22(29):9966-9970
Functionalized 1,2,3‐triazole heterocycles have been known for a long time and hold an extraordinary potential in diverse research areas ranging from medicinal chemistry to material science. However, the scope of therapeutically important 1‐substituted 4‐acyl‐1H‐1,2,3‐triazoles is much less explored, probably due to the lack of synthetic methodologies of good scope and practicality. Here, we describe a practical and efficient one‐pot multicomponent reaction for the synthesis of α‐ketotriazoles from readily available building blocks such as methyl ketones, N,N‐dimethylformamide dimethyl acetal, and organic azides with 100 % regioselectivity. This reaction is enabled by the in situ formation of an enaminone intermediate followed by its 1,3‐dipolar cycloaddition reaction with an organic azide. We effectively utilized the developed strategy for the derivatization of various heterocycles and natural products, a protocol which is difficult or impossible to realize by other means. 相似文献
12.
Xin‐Ping Hui Heng‐Shan Dong Peng‐Fei Xu Zi‐Yi Zhang Qin Wang Yan‐Ni Gong 《中国化学会会志》2000,47(5):1115-1119
The condensation of 4‐amino‐5‐mercapto‐3‐(2‐phenylquinolin‐4‐yl)/3‐(1‐p‐chlorophenyl‐5‐methyl‐1,2,3‐triazol‐4‐yl)‐1,2,4‐triazoles 1a‐b with chloroacetaldehyde 2a‐b , ω‐bromo‐ω‐(1H‐1,2,4‐triazol‐1‐yl)acetophenone 3a‐b , chloranil 4a‐b , 2‐bromocyclohexanone 5a‐b , 2,4′‐dibromoacetophenone 6a‐b and 2‐bromo‐6′‐methoxy‐2′‐acetonaphthone 7a‐b are described. The structures of the compounds synthesized were confirmed by elemental analyses, IR, 1H NMR and mass spectra. The antibacterial activities were also evaluated. 相似文献
13.
1‐Monosubstituted aliphatic 1,2,3‐triazoles were synthesized by a one‐pot reaction from aliphatic halides (Cl and Br), sodium azide and propiolic acid. The yields ranged from moderate to good. The reaction was easily carried out in DMF with Cs2CO3 at 100°C by copper‐catalyzed click cycloaddition/decarboxylation. 相似文献
14.
Latifeh Navidpour Leila Karimi Mohsen Amini Mohssen Vosooghi Abbas Shafiee 《Journal of heterocyclic chemistry》2004,41(2):201-204
Arylation of the readily available 3‐alkythio‐5‐aryl‐1,2,4‐triazoles gave 5‐alkylthio‐1,3‐diaryl‐1,2,4‐triazoles in moderate yield. The structures of the latter were confirmed by NOE and 13C‐NMR. 相似文献
15.
Dr. Jérôme Jacq Dr. Patrick Pasau 《Chemistry (Weinheim an der Bergstrasse, Germany)》2014,20(38):12223-12233
1,2,3‐Triazole has become one of the most important heterocycles in contemporary medicinal chemistry. The development of the copper‐catalyzed Huisgen cycloaddition has allowed the efficient synthesis of 1‐substituted 1,2,3‐triazoles. However, only a few methods are available for the selective preparation of 2‐substituted 1,2,3‐triazole isomers. In this context, we decided to develop an efficient flow synthesis for the preparation of various 2‐aryl‐1,2,3‐triazoles. Our strategy involves a three‐step synthesis under continuous‐flow conditions that starts from the diazotization of anilines and subsequent reaction with malononitrile, followed by nucleophilic addition of amines, and finally employs a catalytic copper(II) cyclization. Potential safety hazards associated with the formation of reactive diazonium species have been addressed by inline quenching. The use of flow equipment allows reliable scale up processes with precise control of the reaction conditions. Synthesis of 2‐substituted 1,2,3‐triazoles has been achieved in good yields with excellent selectivities, thus providing a wide range of 1,2,3‐triazoles. 相似文献
16.
Efficient Atropodiastereoselective Access to 5,5′‐Bis‐1,2,3‐triazoles: Studies on 1‐Glucosylated 5‐Halogeno 1,2,3‐Triazoles and Their 5‐Substituted Derivatives as Glycogen Phosphorylase Inhibitors
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David Goyard Aikaterini S. Chajistamatiou Anastasia I. Sotiropoulou Dr. Evangelia D. Chrysina Dr. Jean‐Pierre Praly Dr. Sébastien Vidal 《Chemistry (Weinheim an der Bergstrasse, Germany)》2014,20(18):5423-5432
Whereas copper‐catalyzed azide–alkyne cycloaddition (CuAAC) between acetylated β‐D ‐glucosyl azide and alkyl or phenyl acetylenes led to the corresponding 4‐substituted 1‐glucosyl‐1,2,3‐triazoles in good yields, use of similar conditions but with 2 equiv CuI or CuBr led to the 5‐halogeno analogues (>71 %). In contrast, with 2 equiv CuCl and either propargyl acetate or phenyl acetylene, the major products (>56 %) displayed two 5,5′‐linked triazole rings resulting from homocoupling of the 1‐glucosyl‐4‐substituted 1,2,3‐triazoles. The 4‐phenyl substituted compounds (acetylated, O‐unprotected) and the acetylated 4‐acetoxymethyl derivative existed in solution as a single form (d.r.>95:5), as shown by NMR spectroscopic analysis. The two 4‐phenyl substituted structures were unambiguously identified for the first time by X‐ray diffraction analysis, as atropisomers with aR stereochemistry. This represents one of the first efficient and highly atropodiastereoselective approaches to glucose‐based bis‐triazoles as single atropisomers. The products were purified by standard silica gel chromatography. Through Sonogashira or Suzuki cross‐couplings, the 1‐glucosyl‐5‐halogeno‐1,2,3‐triazoles were efficiently converted into a library of 1,2,3‐triazoles of the 1‐glucosyl‐5‐substituted (alkynyl, aryl) type. Attempts to achieve Heck coupling to methyl acrylate failed, but a stable palladium‐associated triazole was isolated and analyzed by 1H NMR and MS. O‐Unprotected derivatives were tested as inhibitors of glycogen phosphorylase. The modest inhibition activities measured showed that 4,5‐disubstituted 1‐glucosyl‐1,2,3‐triazoles bind weakly to the enzyme. This suggests that such ligands do not fit the catalytic site or any other binding site of the enzyme. 相似文献
17.
Francesco Paolo Invidiata Stefania Aiello Giancarlo Furno' Enrico Aiello Daniele Simoni Riccardo Rondanin 《Journal of heterocyclic chemistry》2000,37(2):355-361
Thermal rearrangement of 3‐acylisoxazole arylhydrazones allowed facile preparation of 2H‐1,2,3‐triazoles which were firstly reacted with isoamyl nitrite and then with an opportune arylhydrazine to produce the corresponding α‐hydroxyiminohydrazones 8a‐h . The reaction of compounds 8a‐h with phosphorus pentachloride afforded the desired 4,4′‐bitriazoles 1a‐h . The α‐hydroxyiminoketone derivative 7 or the α‐diketone 14 reacted easily with 1,2‐phenylenediamine to afford 1,2,3‐triazoles 2a‐c bearing the quinoxaline moiety at position 4. Improved yields of the quinoxalines 2a‐c were obtained when 1,2‐phenylenediamine was reacted with the dioxime 15. 相似文献
18.
Yuliya V. Filippova Anna G. Sukhanova Sergei V. Voitekhovich Vadim E. Matulis Gennady T. Sukhanov Yury V. Grigoriev Oleg A. Ivashkevich 《Journal of heterocyclic chemistry》2012,49(4):965-968
4‐Nitro‐1,2,3‐triazole was found to react with tert‐butanol in concentrated sulfuric acid to yield 1‐tert‐butyl‐4‐nitro‐1,2,3‐triazole as the only reaction product, whereas tert‐butylation and tritylation of 4‐nitro‐1,2,3‐triazole in presence of catalytic amount of sulfuric acid in benzene was found to provide mixtures of isomeric 1‐ and 2‐alkyl‐4‐nitro‐1,2,3‐triazoles with predominance of N2‐alkylated products. A new methodology for preparation of 1‐alkyl‐5‐nitro‐1,2,3‐triazoles from 1‐tert‐butyl‐4‐nitro‐1,2,3‐triazole via exhaustive alkylation followed by removal of tert‐butyl group from intermediate triazolium salts was demonstrated by the example of preparation of 1‐methyl‐5‐nitro‐1,2,3‐triazole. 相似文献
19.
F. Johari Daha H. Matloubi S. A. Tabatabi B. Shafii A. Shafiee 《Journal of heterocyclic chemistry》2005,42(1):33-37
Condensation of 4‐methylsulfonylaniline with aryl aldehyde in ethanol‐tetrahydrofuran afforded the imino compound 3 . 1,3‐Cycloaddtion of diazomethane with compound 3 followed by oxidazation of the triazoline 4 with potassium permanganate gave 1‐(4‐methylsulfonylphenyl)‐5‐aryl‐1,2,3‐triazoles 5 . Similarly, condensation of 4‐(N,N‐dibenzylaminosulfonyl)aniline with aryl aldehyde followed by 1,3‐cycloaddition of diazomethane with the imino compound 11 and the subsequent oxidation of triazoline 12 with potassium permanganate yielded the triazole 13 . Debenzylation of compound 13 with sulfuric acid gave the desired compound 1‐(4‐aminosulfonylphenyl)5‐aryl‐1,2,3‐triazoles 14 . 相似文献
20.
Dr. Sumith A. Kularatne Dr. Vishal Deshmukh Dr. Jennifer Ma Dr. Virginie Tardif Dr. Reyna K. V. Lim Holly M. Pugh Dr. Ying Sun Anthony Manibusan Aaron J. Sellers Dr. Richard S. Barnett Shailaja Srinagesh Jane S. Forsyth Dr. Wolf Hassenpflug Dr. Feng Tian Dr. Tsotne Javahishvili Prof. Brunhilde Felding‐Habermann Prof. Brian R. Lawson Dr. Stephanie A. Kazane Prof. Peter G. Schultz 《Angewandte Chemie (International ed. in English)》2014,53(44):11863-11867
A chemically defined anti‐CXCR4–auristatin antibody–drug conjugate (ADC) was synthesized that selectively eliminates tumor cells overexpressing the CXCR4 receptor. The unnatural amino acid p‐acetylphenylalanine (pAcF) was site‐specifically incorporated into an anti‐CXCR4 immunoglobulin G (IgG) and conjugated to an auristatin through a stable, non‐cleavable oxime linkage to afford a chemically homogeneous ADC. The full‐length anti‐CXCR4 ADC was selectively cytotoxic to CXCR4+ cancer cells in vitro (half maximal effective concentration (EC50)≈80–100 pM ). Moreover, the anti‐CXCR4 ADC eliminated pulmonary lesions from human osteosarcoma cells in a lung‐seeding tumor model in mice. No significant overt toxicity was observed but there was a modest decrease in the bone‐marrow‐derived CXCR4+ cell population. Because CXCR4 is highly expressed in a majority of metastatic cancers, a CXCR4–auristatin ADC may be useful for the treatment of a variety of metastatic malignancies. 相似文献