- The preparation, characterization and catalytic activity of Ni NPs supported on porous alginate-g-poly(p-styrene sulfonamide-co-acrylamide)
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Herein, we report the synthesis of nickel nanoparticles under mild conditions using porous alginate-g-poly(p-styrene sulfonamide-co-acrylamide) as a protecting/stabilizing agent and sodium borohydride as a reducing agent. The porous cross-linked polymeric support was preparedviacombining the use of sol-gel, nanocasting, and crosslinking techniques, in which thep-styrene sulfonamide monomer (PSSA) andN,N′-methylene-bis (acrylamide) (MBA) cross-linker underwent copolymerization on the surface of sodium alginate in the presence of a SiO2nanoparticle (NP) template (Alg-PSSA-co-ACA). The prepared catalyst (Alg-PSSA-co-ACA@Ni) showed high catalytic activity for the one-step synthesis of 1,3,4-oxadiazoles from the reaction of hydrazides and aryl iodides through isocyanide insertion/cyclization.
- Alavinia, Sedigheh,Ghorbani-Vaghei, Ramin
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p. 29728 - 29740
(2021/10/06)
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- Electrochemical Synthesis of 2,5-Disubstituted 1,3,4-Oxadiazoles from α-Keto Acids and Acylhydrazines Under Mild Conditions
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1,3,4-Oxadiazoles are a kind of useful heterocycles which can be frequently found in materials and bioactive molecules. In this study, intermolecular electrochemical cyclization between α-keto acids and acylhydrazines has been developed for the synthesis of 2,5-disubstituted 1,3,4-oxadiazoles with the yield up to 91 %. This transformation can be run under mild reaction conditions in the absence of external oxidant, base and transition metal catalyst. Both symmetrical and unsymmetrical 2,5-disubstituted 1,3,4-oxadiazoles could be prepared according to the careful choice of the substrate combination. Gram scale synthesis also illustrates the potential application of this protocol in large preparation.
- Lu, Fangling,Gong, Fengping,Li, Liangsen,Zhang, Kan,Li, Zhen,Zhang, Xinwei,Yin, Ying,Wang, Ying,Gao, Ziwei,Zhang, Heng,Lei, Aiwen
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supporting information
p. 3257 - 3260
(2020/05/25)
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- TiCl4 mediated facile synthesis of 1,3,4-oxadiazoles and 1,3,4-thiadiazoles
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An efficient method for the synthesis of 2,5-disubstituted 1,3,4-oxadiazoles and 1,3,4-thiadiazoles has been developed. Various hydrazides or thionyl hydrazides readily react with DMA derivatives in the presence of TiCl4 as a catalyst to afford the desired products. This protocol provides a simple and economical procedure that affords the target products with good yields and wide substrate scope.
- Zhang, Lin,Yu, Yu,Tang, Qiang,Yuan, Jianyong,Ran, Dongzhi,Tian, Binghua,Pan, Tao,Gan, Zongjie
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p. 423 - 431
(2019/12/27)
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- Sodium hypochlorite-mediated synthesis of 2,5-disubstituted 1,3,4-oxadiazoles from hydrazides and aldehydes
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[Figure not available: see fulltext.] A simple and convenient method for the synthesis of 2,5-disubstituted 1,3,4-oxadiazoles has been developed. Structurally divergent symmetrical and unsymmetrical 2,5-disubstituted 1,3,4-oxadiazoles can be obtained in moderate to high yields via NaOCl-mediated oxidative cyclization of N-acylhydrazones, generated in situ from aliphatic and aromatic hydrazides and aldehydes.
- Paidi, Karuna Raman,Kolli, Murali Krishna,Reddy, Eeda Koti,Pedakotla, Venkata Ramana
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p. 371 - 376
(2020/05/04)
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- Rescuing the CFTR protein function: Introducing 1,3,4-oxadiazoles as translational readthrough inducing drugs
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Nonsense mutations in the CFTR gene prematurely terminate translation of the CFTR mRNA leading to the production of a truncated protein that lacks normal function causing a more severe form of the cystic fibrosis (CF) disease. About 10% of patients affected by CF show a nonsense mutation. A potential treatment of this alteration is to promote translational readthrough of premature termination codons (PTCs) by Translational Readthrough Inducing Drugs (TRIDs) such as PTC124. In this context we aimed to compare the activity of PTC124 with analogues differing in the heteroatoms position in the central heterocyclic core. By a validated protocol consisting of computational screening, synthesis and biological tests we identified a new small molecule (NV2445) with 1,3,4-oxadiazole core showing a high readthrough activity. Moreover, we evaluated the CFTR functionality after NV2445 treatment in CF model systems and in cells expressing a nonsense-CFTR-mRNA. Finally, we studied the supramolecular interactions between TRIDs and CFTR-mRNA to assess the biological target/mechanism and compared the predicted ADME properties of NV2445 and PTC124.
- Pibiri, Ivana,Lentini, Laura,Melfi, Raffaella,Tutone, Marco,Baldassano, Sara,Ricco Galluzzo, Paola,Di Leonardo, Aldo,Pace, Andrea
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p. 126 - 142
(2018/10/05)
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- Photocatalyzed facile synthesis of 2,5-diaryl 1,3,4-oxadiazoles with polyaniline-?g-C3N4-TiO2 composite under visible light
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PANI (polyaniline)-g-C3N4-TiO2 composite was prepared and found to be efficient for the synthesis of 2,5-diaryl 1,3,4-oxadiazoles under visible light. This reaction involved decarboxylation and cyclization from α-keto acids with acylhydrazines, and a broad scope of substrates were tolerated to provide the desired products in moderate to good yields. Control experiments indicated that a radical pathway was involved in the present photocatalytic reaction and a synergistic effect may exist in the ternary composite. Moreover, this semiconductor photocatalyst could be readily recovered and showed good reusability with only slight decrease in the catalytic activity after six consecutive runs.
- Wang, Liang,Wang, Yaoyao,Chen, Qun,He, Mingyang
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supporting information
p. 1489 - 1492
(2018/03/13)
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- Iron(III)/TEMPO-Catalyzed Synthesis of 2,5-Disubstituted 1,3,4-Oxadiazoles by Oxidative Cyclization under Mild Conditions
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A simple and efficient cationic Fe(III)/TEMPO-catalyzed oxidative cyclization of aroyl hydrazones has been developed for the synthesis of 2,5-disubstituted 1,3,4-oxadiazole derivatives. The reaction offers a broad scope, good functional-group tolerance, and high yields under mild conditions in the presence of O 2.
- Zhang, Guofu,Yu, Yidong,Zhao, Yiyong,Xie, Xiaoqiang,Ding, Chengrong
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p. 1373 - 1377
(2017/06/27)
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- Ligand-free Cu(ii)-mediated aerobic oxidations of aldehyde hydrazones leading to N,N′-diacylhydrazines and 1,3,4-oxadiazoles
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A Cu(ii)-mediated synthesis of N,N′-diacylhydrazines and 1,3,4-oxadiazoles from aldehyde hydrazones has been developed. This is the first time that the synthesis of N,N′-diacylhydrazines and 1,3,4-oxadiazoles using N,N-dimethylamides as the acylation reagent and O2 in air as the oxidation reagent is reported. These reactions offered several advantages including simple workups, ligand-free inexpensive metal salts as mediators, high yields, and wide scope of substrates.
- Liu, Lei,Feng, Suliu
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supporting information
p. 2585 - 2592
(2017/04/03)
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- A process for preparing 2, 5 - disubstituted - 1, 3, 4 - oxadiazoles (by machine translation)
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The invention provides a method for catalytic oxidative cyclization of formula (II) is shown in the 1, 3, 4 - oxadiazole method, said method comprising: in order to having a structure of formula (I) indicated by the formyl zong compound as a raw material, in order to air or oxygen atmosphere, in order to nitric acid the iron is catalyst, in order to 2, 2, 6, 6 - tetramethyl piperidine nitrogen oxides as initiator, under the action of the water absorbing agent, under the action of the water absorbing agent, in an organic solvent, for 25 - 60 °C lower reaction 3 - 12h, and the resulting reaction solution by the following formula (II) after treatment indicated by the 1, 3, 4 - oxadiazole compounds; the reaction of the invention speed, mild condition, easy operation, low cost, safe reaction, the whole process is friendly to the environment, pollution-free. (by machine translation)
- -
-
Paragraph 0031; 0032; 0033; 0034; 0035; 0036-0040
(2017/07/19)
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- Palladium-Catalyzed Aminocarbonylation Reaction to Access 1,3,4-Oxadiazoles using Chloroform as the Carbon Monoxide Source
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A palladium-catalyzed aminocarbonylation reaction of aryl halides with chloroform and tetrazoles has been developed, where chloroform was employed as the carbon monoxide (CO) source in the presence of cesium hydroxide. The in situ generated N-acylated tetrazoles were unstable and easily decomposed to afford 2,5-disubstituted 1,3,4-oxadiazoles. A wide range of tetrazoles and aryl halides reacted smoothly under the optimized reaction conditions to give the corresponding products in moderate to good yields.
- Li, Zhengyi,Wang, Liang
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p. 3469 - 3473
(2016/01/25)
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- Palladium-catalyzed one-pot synthesis of diazoles via tert-butyl isocyanide insertion
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An efficient one-pot palladium-catalyzed reaction for the synthesis of diazoles from readily available hydrazides and aryl halide via isocyanide insertion/cyclization sequence has been developed. This methodology efficiently constructs diazoles in good to excellent yields with the advantages of wide functional group tolerance and operational simplicity.
- Fan, Xiang-Yuan,Jiang, Xiao,Zhang, Ying,Chen, Zhen-Bang,Zhu, Yong-Ming
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p. 10402 - 10408
(2015/10/28)
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- Organocatalytic Oxidative Amidation of Aldehydes with Tetrazoles to Construct 2,5-Diaryl 1,3,4-Oxadiazoles
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A practical and metal-free oxidative amidation of aldehydes with tetrazoles into 1,3,4-oxadiazoles has been developed by employing tetrabutylammonium iodide (TBAI) as catalyst and tert-butyl hydroperoxide (TBHP) as oxidant. A wide range of 2,5-disubstituted 1,3,4-oxadiazoles can be conveniently generated in moderate to good yields. Gram-scale reaction was also realized in this catalytic system..
- Cao, Jing,Wang, Liang
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supporting information
p. 1239 - 1243
(2015/11/27)
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- One-Pot Synthesis of 2,5-Diaryl 1,3,4-Oxadiazoles via Di-tert-butyl Peroxide Promoted N-Acylation of Aryl Tetrazoles with Aldehydes
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A metal- and base-free protocol for one-pot synthesis of 2,5-diaryl 1,3,4-oxadiazoles via a radical-promoted cross-dehydrogenative coupling strategy was developed. This reaction involved the N-acylation of aryl tetrazoles with aryl aldehydes, followed by thermal rearrangement. A wide range of aryl tetrazoles and aryl aldehydes survived the reaction conditions to deliver the corresponding products in moderate to good yields. (Chemical Equation Presented).
- Wang, Liang,Cao, Jing,Chen, Qun,He, Mingyang
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supporting information
p. 4743 - 4748
(2015/05/13)
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- In situ generated cetyltrimethylammonium bisulphate in choline chloride-urea deep eutectic solvent: A novel catalytic system for one pot synthesis of 1,3,4-oxadiazole
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Cetyltrimethylammonium bisulphate ([CTA]HSO4) catalysed one pot synthesis of 2,5-disubstituted-1,3,4-oxadiazoles from carboxylic acid and acid hydrazide in biodegradable deep eutectic solvent is investigated. [CTA]HSO 4 is generated in situ from cetyltrimethylammonium peroxodisulphate. Cyclization of diacylhydrazide using [CTA]HSO4 gives best alternative to traditional dehydration agents. Its remarkable features include a milder procedure, simplicity in workup and purification, good to excellent yields of products, use of inexpensive, recyclable reagents, and eco-friendly aspects by avoiding toxic catalysts/reagents and solvents. Graphical Abstract: [Figure not available: see fulltext.].
- More, Priyanka Anant,Gadilohar, Balu Laxman,Shankarling, Ganapati Subray
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p. 1393 - 1398
(2014/08/18)
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- C-H arylation of azaheterocycles: A direct ligand-free and Cu-catalyzed approach using diaryliodonium salts
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An efficient and high yielding Cu-catalyzed direct C-H arylation of azaheterocycles including oxadiazoles, thiadiazoles, benzoxazoles and benzothiazoles has been achieved by employing easily accessible diaryliodonium salts. the Partner Organisations 2014.
- Kumar, Dalip,Pilania, Meenakshi,Arun,Pooniya, Savita
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supporting information
p. 6340 - 6344
(2014/08/18)
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- Iodine-catalysed oxidative cyclisation of acylhydrazones to 2,5-substituted 1,3,4-oxadiazoles
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An environmentally benign synthesis of 2,5-disubstituted 1,3,4-oxadiazoles has been developed starting from N-aroylhydrazones and N-acetylhydrazones at room or ambient temperature using a catalytic quantity of iodine in the presence of an aqueous hydrogen peroxide oxidant.
- Majji, Ganesh,Rout, Saroj Kumar,Guin, Srimanta,Gogoi, Anupal,Patel, Bhisma K.
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p. 5357 - 5362
(2014/01/23)
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- 17O NMR studies of substituted 1,3,4-oxadiazoles
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Three series of substituted 1,3,4-oxadiazoles were studied by 17O NMR spectroscopy. Chemical shifts values were correlated with empirical Hammett parameters as well as calculated bond lengths and chemical shielding values.
- Gierczyk, Blazej,Zalas, MacIej,Kazmierczak, Marcin,Grajewski, Jakub,Pankiewicz, Radoslaw,Wyrzykiewicz, Bozena
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experimental part
p. 648 - 654
(2012/01/06)
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- Cu(II) catalyzed imine C-H functionalization leading to synthesis of 2,5-substituted 1,3,4-oxadiazoles
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A direct access to symmetrical and unsymmetrical 2,5-disubstituted [1,3,4]-oxadiazoles has been accomplished through an imine C-H functionalization of N-arylidenearoylhydrazide using a catalytic quantity of Cu(OTf)2. This is the first example of amidic oxygen functioning as a nucleophile in a Cu-catalyzed oxidative coupling of an imine C-H bond. These reactions can be performed in air atmosphere and moisture making it exceptionally practical for application in organic synthesis.
- Guin, Srimanta,Ghosh, Tuhin,Rout, Saroj Kumar,Banerjee, Arghya,Patel, Bhisma K.
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supporting information; experimental part
p. 5976 - 5979
(2012/01/02)
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- Bipolar molecules with high triplet energies: Synthesis, photophysical, and structural properties
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This article sheds new light on the interplay of electronic and conformational effects in luminescent bipolar molecules. A series of carbazole/1,3,4-oxadiazole hybrid molecules is described in which the optoelectronic properties are systematically varied by substituent effects which tune the intramolecular torsion angles. The synthesis, photophysical properties, cyclic voltammetric data, X-ray crystal structures, and DFT calculations are presented. Excited state intramolecular charge transfer (ICT) is observed from the donor carbazole/2,7-dimethoxycarbazole to the acceptor phenyl/diphenyloxadiazole moieties. Introducing more bulky substituents onto the diphenyloxadiazole fragment systematically increases the singlet and triplet energy levels (ES and ET) and blue shifts the absorption and emission bands. The triplet excited state is located mostly on the oxadiazole unit. The introduction of 2,7-dimethoxy substituents onto the carbazole moiety lowers the value of ES, although ET is unaffected, which means that the singlet-triplet gap is reduced (for 7bE S - ET = 0.61 eV). A strategy has been established for achieving unusually high triplet levels for bipolar molecules (ET = 2.64-2.78 eV at 14 K) while at the same time limiting the increase in the singlet energy.
- Zheng, Yonghao,Batsanov, Andrei S.,Jankus, Vygintas,Dias, Fernando B.,Bryce, Martin R.,Monkman, Andrew P.
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scheme or table
p. 8300 - 8310
(2011/12/04)
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- Copper-mediated direct arylation of 1,3,4-oxadiazoles and 1,2,4-triazoles with aryl iodides
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The copper-mediated direct arylation of 1,3,4-oxadiazoles and 1,2,4-triazoles with aryl iodides proceeds efficiently in the presence of suitable ligands and bases. This method allows the installation of a variety of aryl moieties bearing a functional group such as ketone, ester, or nitrile so as to enable the facile construction of various functionalized oxadiazole and triazole core π systems.
- Kawano, Tsuyoshi,Yoshizumi, Tomoki,Hirano, Koji,Satoh, Tetsuya,Miura, Masahiro
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supporting information; experimental part
p. 3072 - 3075
(2009/12/06)
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- Greener and rapid access to bio-active heterocycles: one-pot solvent-free synthesis of 1,3,4-oxadiazoles and 1,3,4-thiadiazoles
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A novel one-pot solvent-free synthesis of 1,3,4-oxadiazoles and 1,3,4-thiadiazoles by condensation of acid hydrazide and triethyl orthoalkanates under microwave irradiations is reported. This green protocol was catalyzed efficiently by solid supported NafionNR50 and phosphorus pentasulfide in alumina (P4S10/Al2O3) with excellent yields.
- Polshettiwar, Vivek,Varma, Rajender S.
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p. 879 - 883
(2008/09/17)
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- Oxidative cyclization of aromatic aldehyde n-acylhydrazones by bis(trifluoroacetoxy)iodobenzene
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Aromatic aldehyde N-acylhydrazones were oxidized into 2,5-disubstituted 1,3,4-oxadiazoles with bis(trifluoroacetoxy)iodobenzene in CHCl3 or DMSO at room temperature in good to excellent yields. Copyright Taylor & Francis Group, LLC.
- Shang, Zhenhua
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p. 2927 - 2937
(2007/10/03)
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- Oxydations d'hydrazones par le bioxyde de plomb: nouvelles syntheses d'oxadiazoles-1,3,4 et de derives de l'amino-4 triazol-1,2,4 one-5
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Aromatic aldehyde aroylhydrazones when oxidized with lead dioxide, in acetic acid, gave quickly the corresponding 1,3,4-oxadiazoles in good yields.Aromatic aldehyde carbodihydrazones on the other hand, gave derivatives of 4-amino-3-aryl-1,2,4-triazol-5-ones, in dimethylformamide as solvent.To explain these results, some radical mechanisms are proposed.
- Milcent, Rene,Barbier, Geo
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