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1.
A series of novel dispiropyrrolidine-linked 1,2,3-triazole derivatives have been prepared by one-pot, four-component protocol that employed 5-arylidene-3-(prop-2-ynyl)thiazolidine-2,4-dione, isatin, sarcosine and substituted azides using Cu(I) generated in situ as catalyst in PEG-400 as a highly efficient and green media. This is the first report of a four-component reaction involving a classical Huisgen reaction, in which the two dipolar moieties (substituted azides and in situ generated azomethine ylides) react with acetylenic and olefinic dipolarophiles, respectively. The 1,3-dipolar cycloaddition proceeds in a highly regio- and stereo-selective manner. This methodology can be an ideal tool for the preparation of biologically important five-membered heterocyclic compounds in one pot. 相似文献
2.
In the present study, following a one-pot two-step protocol, we have synthesized novel sulfonamides-isoxazolines hybrids (3a-r) via a highly regioselective 1,3-dipolar cycloaddition. The present methodology capitalized on trichloroisocyanuric acid (TCCA) as a safe and ecological oxidant and chlorinating agent for the in-situ conversion of aldehydes to nitrile oxides in the presence of hydroxylamine hydrochloride, under ultrasound activation. These nitrile oxides could be engaged in 1,3-dipolar cycloaddition reactions with various alkene to afford the targeted sulfonamides-isoxazolines hybrids (3a-r). The latter were assessed for their antineoplastic activity against model leukemia cell lines (Chronic Myeloid Leukemia, K562 and Promyelocytic Leukemia, HL-60). 相似文献
3.
Poly (ADP-ribose) polymerase (PARP-1) is a well-established nuclear protein with prominent role in signaling and DNA repair. Various clinical candidates have been identified with the role in PARP-1 inhibition. Based on the pharmacophoric features identified from previous studies and molecular docking interactions, thiazolidine-2,4-dione derivatives have been evaluated for their PARP inhibitory activity. From an in vitro assay, 5-((1-(4-isopropylbenzyl)-1H-indol-3-yl)methylene)thiazolidine-2,4-dione (16) was identified as a potent inhibitor having low micromolar inhibitory activity \((\hbox {IC}_{50} \,{=}\, 0.74 \,\pm \, 0.25\,\upmu \hbox {M})\). Thus, a structure-based design approach utilized in the present study helped to identify thiazolidine-2,4-dione as a novel scaffold against PARP-1 for potential development of potent anticancer therapeutics. 相似文献
4.
Solid-phase methods are of a great significance in organic synthesis. Recent developments of these methods are providing new ways to construct libraries of small organic molecules. Five-membered heterocyclic compounds, which can be utilized in a variety of applications, are formed in the 1,3-dipolar cycloaddition reaction between dipolarophiles and dipoles. This review deals with the solid-phase synthesis of heterocycles via [3+2] cycloaddition reaction. Cycloaddition reactions of polymer-bound dipoles and polymer-bound dipolarophiles and intramolecular solid-phase cycloadditions are discussed in separate sections. Reactions of dipolarophiles such as alkenes, alkynes, and imines with dipoles such as azomethine ylides, azomethine imines, nitrile imines, azides, nitrones, and nitrile oxides are described. The recent literature up to December 2003 is covered. 相似文献
5.
Jadidi K Gharemanzadeh R Mehrdad M Darabi HR Khavasi HR Asgari D 《Ultrasonics sonochemistry》2008,15(2):124-128
Novel pyrrolizidines (1) were synthesized from 1,3-dipolar cycloaddition of azomethine ylides and dipolarophiles (4). The reactions were highly diastereoselective and regioselective and were carried out under reflux and ultrasonic condition at room temperature. In general, milder conditions and moderate improvements in rates and reaction times were observed when ultrasonic condition was used. The products were obtained in high yields, and their structures were determined by (1)H and (13)C NMR spectral data and X-ray diffraction. 相似文献
6.
Victoria de la Sovera Ana Bellomo Jesus M. Pena David Gonzalez Hélio A. Stefani 《Molecular diversity》2011,15(1):163-172
The palladium catalyzed cross-coupling reaction of phenyltrifluoroborate with a chemoenzymatically derived bromoazidoconduritol,
combined with 1,3-dipolar cycloaddition, with a variety of alkynes is described. Fourteen new compounds were synthesized in
moderate to good yields. The click chemistry reaction can be effected by using sodium ascorbate and CuSO4 · 5H2O as catalyst in toluene–H2O at room temperature. 相似文献
7.
Investigations of the inhibition of copper corrosion in nitric acid solutions by ketene dithioacetal derivatives 总被引:1,自引:0,他引:1
Ketene dithioacetal derivatives, namely 3-[bis(methylthio)methylene] pentane-2,4-dione (1), 3-(1,3-dithian-2-ylidene) pentane-2,4-dione (2) and 3-(1,3-dithiolan-2-ylidene) pentane-2,4-dione (3) were synthesized and their respective capacity to inhibit copper corrosion in 3 M HNO3 was investigated by means of weight loss, potentiodynamic polarization, scanning electron microscopy (SEM) and energy dispersive X-ray fluorescence (XRF). The obtained results indicate that the addition of these compounds significantly decreases the corrosion rate. Potentiodynamic polarization studies clearly showed that the inhibition efficiency increases with increasing concentration of the investigated compounds at a fixed temperature, but decreases with increasing temperature. These results on the whole showed that the studied substances are good cathodic inhibitors for copper corrosion in nitric acid medium. SEM and energy dispersive X-ray (EDAX) examination of the copper surface revealed that these compounds prevented copper from corrosion by adsorption on its surface to form a protective film, which acts as a barrier to aggressive agents. The presence of these organic compounds adsorbed on the electrode surface was confirmed by XRF investigations. 相似文献
8.
A facile and efficient one-pot three-component procedure for synthesis of novel dispirooxindolecyclo[pyrrolo[1,2-c]thiazole-6,5′-thiazolidine] derivatives without any catalysts under ultrasonic condition has been developed. Combining with the advantages of sonochemistry, such as mild reaction conditions, good yield and short reaction times, we have made a progress on construction of novel disiproheterocyclic compounds via the 1,3-dipolar cycloaddition of azomethine ylides. Several experiments were especially carried out for investigating the acceleration mechanism of ultrasound on the cycloaddition. 相似文献
9.
Ultrasonic-assisted synthesis of chrysin derivatives linked with 1,2,3-triazoles by 1,3-dipolar cycloaddition reaction 总被引:1,自引:0,他引:1
The 1,3-dipolar cycloaddition reaction between 7-(3-azidopropoxy)-5-hydroxyflavone and phenylacetylene was carried out to investigate the synthesis of 7-(3-(4-phenyl-1,2,3-triazol-1-yl)propoxy)- 5-hydroxyflavone in presence of ultrasound (sono-synthesis) and absence of ultrasound (conventional method) under relatively optimized solvent and catalyst conditions. The reaction rate was notably accelerated with the help of ultrasound irradiation. An experiment was especially carried out for investigating the acceleration mechanism of ultrasound on the cycloaddition. A novel series of chrysin derivatives linked with 1,2,3-triazoles were obtained by the copper(I)-catalyzed 1,3-dipolar Huisgen cycloaddition reaction using t-BuOH/H(2)O (1:1 v/v) as reaction solvents and CuSO(4)·5H(2)O/sodium ascorbate as the catalyst at room temperature in the presence of ultrasound irradiation. Their structures are elucidated by NMR, ESI MS, IR and Elemental analysis. 相似文献
10.
Abubakar M. Ngaski 《光谱学快报》2013,46(3):214-216
The rhodium(II) acetate [Rh2(OAc4)]-catalyzed reaction of ethyl diazoacetate with N-methylisatin leads to the formation of diastereomeric oxiranes spiro-fused to N-methyl-2-oxindole together with 1,3-dioxolane bis-spiro-fused to N-methyl-2-oxindole. The formation of ylide from the reaction of rhodium-carbenoid with C-3 carbonyl group of the N-methylisatin undergoing a 1,3-cyclization, and a [3 + 2]-dipolar cycloaddition with another molecule of N-methylisatin, respectively, explains the formation of products. The application of nuclear overhauser effect spectroscopy to determine the E–Z-configurations of the spiro-oxirane-oxindoles is demonstrated. 相似文献
11.
《Current Applied Physics》2007,7(1):96-101
Five dimethylindium complexes of type Me2InL [L = N-(4-methoxy)benzylidenethiobenzahydrazonato (1), N-(3,4-dimethoxy)benzylidenethiobenzahydrazonato (2), N-(4-N,N-dimethylamino)benzylidenethiobenzahydrazonato (3), N-(2-naphthyl)methylene thiobenzahydrazonato (4) and N-(9-anthryl)methylenethiobenzahydrazonato (5)] have been synthesized by reaction of trimethylindium with appropriate N-arylmethylenethiobenzahydrozones. The complexes obtained have been characterized by elemental analysis, 1H NMR, IR and mass spectroscopy. Compounds 1–5 emit blue colors at λmax = 432–479 nm when irradiated by UV light. The electroluminescent (EL) properties of 1–5 were examined by fabricating EL devices using 1–5 as emitter, respectively. The EL bands are located in the green region (513–578 nm). 相似文献
12.
《Ultrasonics sonochemistry》2014,21(2):612-619
In the present study, kinetics of synthesis of 2,2-di(prop-2-ynyl)-1H-indene-1,3(2H)-dione was successfully carried out by propargylation of indene-1,3-dione with propargyl bromide using aqueous potassium hydroxide and catalyzed by a newly synthesized phase-transfer catalyst viz., N-benzyl-N-ethyl-N-isopropylpropan-2-ammonium bromide, PTC under ultrasonic (40 kHz, 300 W) assisted organic solvent condition. The pseudo first-order kinetic equation was applied to describe the overall reaction. Under ultrasound irradiation (40 kHz, 300 W) in a batch reactor, it shows that the overall reaction rate can be greatly enhanced with ultrasound irradiation than without ultrasound. 相似文献
13.
Thangaraj Arasakumar Sadasivam Mathusalini Athar Ata Ramasamy Shankar Subashini Gopalan Krishnasamy Lakshmi Pandiyarajan Sakthivel Palathurai Subramaniam Mohan 《Molecular diversity》2017,21(1):37-52
A series of 4-quinolone-3-carboxylic acid-containing spirooxindole-pyrrolidine derivatives was synthesized via multicomponent 1,3-dipolar cycloaddition reactions of azomethine ylides with new (E)-4-oxo-6-(3-phenyl-acryloyl)-1,4-dihydroquinoline-3-carboxylic acids in good yields with high regioselectivity. The cycloadducts were characterized by analytical and spectral data including \(^{1}\hbox {H}\), \(^{13}\hbox {C}\), 2D NMR and mass spectroscopy. The structure of one of the compounds (8a) was investigated theoretically by computational techniques. DFT studies support the proposed mechanism for this cycloaddition reaction. Furthermore, antibacterial activities of the new compounds were evaluated against Gram-positive and Gram-negative bacterial strains. Compounds 8f, 8m and 8p showed potent inhibition activities against selected bacteria. The in vitro cytotoxicity of spirooxindole derivatives (8a–r) was evaluated against MCF-7 breast cancer cell line. Among the various compounds tested, compound 8f \((\hbox {IC}_{50} = 18.35~\upmu \hbox {M})\) showed significant cytotoxic activity compared to the standard drug doxorubicin \((\hbox {IC}_{50 }= 15.00~\upmu \hbox {M})\). 相似文献
14.
Twenty ester-linked 1,4-disubstituted 1,2,3-triazoles having a furyl/thienyl moiety have been synthesized from heteroaryl prop-2-yn-1-yl carboxylate and aromatic azides via a Cu(I) catalyzed 1,3-dipolar cycloaddition. All the synthesized compounds were characterized by FTIR, \(^{1}\)H NMR, \(^{13}\)C NMR spectroscopy and HRMS. Synthesized triazoles were tested in vitro for antimicrobial evaluation against Gram-negative bacteria—Escherichia coli, Enterobacter aerogenes and Klebsiella pneumoniae; Gram-positive bacteria—Staphylococcus aureus and two fungal strains—Candida albicans and Aspergillus niger, reflecting moderate to good activity. The structure of compound 6f was also confirmed by X-ray crystallography (CCDC 1469326). 相似文献
15.
An efficient synthesis of 1,4-disubstituted 1,2,3-triazole derivatives was studied. 1,4-Disubstituted 1,2,3-triazoles containing isoxazole and thymidine structures were synthesized in 84–96% yields starting from various terminal isoxazole ether alkynes and β-thymidine azide derivatives via a 1,3-dispolar cycloaddition using copper acetate, sodium ascorbate as the catalyst under ultrasonic assisted condition. All the target compounds were characterized by HRMS, FT-IR, 1H NMR and 13C NMR spectroscopy. Furthermore, the quorum sensing inhibitory activities of synthesized compounds were evaluated with Chromobacterium violaceum (C. Violaceum CV026) based on their inhibition of violacein production, with compound C10-HSL as a positive control. The compounds 8a, 8c and 8f exhibited considerable levels of inhibitory activity against violacein production, and IC50 values were 217 ± 19, 223 ± 20 and 42.8 ± 4.5 μM, respectively, which highlighted the potential of these compounds as lead structures for further research towards the development of novel QS inhibitors. 相似文献
16.
《Journal of Physics and Chemistry of Solids》2004,65(2-3):349-353
Methanofullerene derivatives C60(CCl2) (1a), C60(CBr2) (1b), C60(CI2) (1c) and C121 (2) were synthesized in 55–84% yields by dehalogenation of the corresponding α-polyhalides via sodium hydroxide, magnesium, respectively, followed by the in situ reaction with fullerene under the irradiation of ultrasound in a non-conventional reaction media, ionic liquid 1-butyl-3-methylimidazolium tetrafluoroborate, [BMIM][BF4]. Only single [6,6]-ring junction cycloaddition isomers of the products were detected in the reaction solutions under our conditions. In contrast, low yields of 6–21% were obtained when the same reactions were operated in tetrahydrofuran. All of the products were purified with HPLC and characterized by 13C NMR and FAB-MS. 相似文献
17.
《Ultrasonics sonochemistry》2014,21(4):1417-1423
Reversible crystal-to-crystal transformations of 3D lead(II) coordination polymers with the ligand 2,5-bis(4-pyridyl)-3,4-diaza-2,4-hexadiene (4-bpdh), from nitrate analoge [Pb(4-bpdh)(NO3)2(H2O)]n (1) to [Pb(4-bpdh)(NO3)(Br)]n (2), [Pb(4-bpdh)(Br)2]n (3), [Pb(4-bpdh)(NO3)(Cl)]n (4) and [Pb(4-bpdh)(Cl)2]n (5) by solid state anion-replacement processes under mechanochemical reactions, have been studied. The reversible solid state structural transformations of compounds 1–5, by anion-replacement processes under mechanochemical reaction, have been verified by PXRD measurements. Nanoparticles of compounds were synthesized by sonochemical process and characterized by scanning electron microscopy (SEM), powder X-ray diffraction, IR spectroscopy and elemental analyses. The SEM images showed that morphology change occurs during solid state anion-replacements of nanocrystals. 相似文献
18.
Photophysical properties of a series of high luminescent europium complexes with fluorinated ligands
Jiangbo Yu 《Journal of luminescence》2011,131(2):328-335
A series of high luminescent europium complexes have been synthesized, such as Eu(TFNB)3phen (1), Eu(PFNP)3phen (2), Eu(HFNH)3phen (3) and Eu(PFND)3phen (4), which have β-diketone ligands containing fluorinated alkyl chains with different lengths and conjugated naphthyl groups, i.e., 4,4,4-trifluoro-1-(2-naphthyl)butane-1,3-dione (TFNB); 4,4,5,5,5-pentafluoro-1-(2-naphthyl)pentane-1,3-dione (PFNP); 4,4,5,5,6,6,6-heptafluoro-1-(2-naphthyl)hexane-1,3-dione (HFNH) and 4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-pentadecafluoro-1-(2-naphthyl)decane-1,3-dione (PFND). And 10-phenanthroline (phen) is coordinated as the neutral second ligand in 1-4. The crystal structures of 1 and 2 have been studied, which are typical and similar to that of 3. The results of TGA-DTA suggest that these Eu complexes have good thermal stabilities. By means of absorption and (time resolved) emission spectroscopy including determination of luminescence quantum yields, energy transfer dynamics and so on, the following results have been obtained: first, these Eu complexes show characteristic pure red color photoluminescence emission with high quantum efficiencies from the central Eu3+ ions through the excitation of the ligands; secondly, photophysical properties of 1, 2, 3 and 4, especially the lifetimes of excited states 5D0 of Eu3+ ions and quantum efficiencies are influenced by the different lengths of fluorinated alkyl chains, though the singlets (S1) and triplets (T1) of the fluorinated ligands are almost the same. 相似文献
19.
In the presence of pyridine, naturally occurring acetylenic spiroketals isolated from Chinese Artemisia species underwent regio and stereoselectively 1,3-dipolar cycloaddition reactions with diazomethane. The structures of the adducts and the regio and stereoselectivity were established mainly by 1D and 2D NMR techniques. This is the first report concerning the 1,3-dipolar cycloaddition reaction of diazomethane to α,β-unsaturated ketals which is of utility in the structure modification of some organic compounds. 相似文献
20.
A novel tetracyclic frameworks of dispiropyrrolizidines can be obtained in moderate to good yields via the 1,3-dipolar cycloaddition of azomethine ylides with dipolarophiles derived from aza-Claisen rearrangement of Baylis-Hillman amines. The transformations are highly regioselective and stereoselective, affording the desired compounds in reduced time and increased yields under ultrasound irradiation at room temperature. All the products are confirmed by 1H, 13C NMR, IR and MS spectra, while their molecular structures are elucidated by X-ray crystallography of a selected sample. 相似文献