1090-82-0Relevant academic research and scientific papers
Zirconium(IV) chloride mediated cyclodehydration of 1,2-diacylhydrazines: A convenient synthesis of 2,5-diaryl 1,3,4-oxadiazoles
Sharma,Begum, Asra,Rakesh,Krishna, Palakodety Radha
, p. 2387 - 2391 (2004)
Zirconium(IV) chloride was invented as a mild catalyst for the cyclodehydration of 1,2-diacylhydrazines. Efficient synthesis of several 2,5-disubstituted 1,3,4-oxadiazoles is reported.
Structural effect on controllable resistive memory switching in donor-acceptor polymer systems
Wang, Kun-Li,Liu, Gang,Chen, Po-Hao,Pan, Liang,Tsai, Hsin-Luen
, p. 322 - 336 (2014)
Controllable bistable electrical conductivity switching behavior and resistive memory effects have been demonstrated in Al/polymer/indium-tin oxide (ITO) sandwich structure devices, constructed from non-conjugated vinyl copolymers of PTPAnOXDm with pendant donor-acceptor chromophores. The observed electrical bistability can be attributed to the field-induced intra- and intermolecular charge transfer interaction between triphenylamine electron donor (D) and oxadiazole electron acceptor (A) entities, and is highly dependent on the chemical structure of the copolymers. The vinyl copolymers showed different memory behaviors, which depended on the loading of D/A ratios. The polymers containing only donor or acceptor moieties showed as insulators, the polymers containing both donor and acceptor moieties showed as WORM, flash and DRAM as D/A ratio increased. The structural effect on the physicochemical and electronic properties of the PTPAnOXDm copolymers, viz surface morphology, thermal stability, optical absorbance and photoluminescence, and molecular orbital energy levels, were investigated systematically to study the factors that influence the memory characteristics of the devices.
One-pot, three component synthesis of 2,5-disubstituted 1,3,4-oxadiazoles catalyzed by heteropolyacid
Heravi, Majid M.,Zadsirjan, Vahideh,Bakhtiari, Khadijeh,Bamoharram, Fatemeh F.
, p. 259 - 263 (2013)
H6[PMo9V3O40] was used as an efficient catalyst for the preparation of 1-aroyl-2-arylidene hydrazines. 2,5-Disubstituted 1,3,4-oxadiazoles have been synthesized by oxidation of 1-aroyl-2-arylidene hydrazines with CrO3 in excellent yields.
Microwave assisted syntheses of 2,5-disubstituted 1,3,4-oxadiazoles
Rostamizadeh, Shahnaz,Housaini, S.A. Ghasem
, p. 8753 - 8756 (2004)
2,5-Di-substituted 1,3,4-oxadiazoles have been synthesized from the oxidation of 1-aroyl-2-arylidene hydrazines with potassium permanganate on the surface of solid mineral support as well as in the mixture of acetone and water under microwave irradiation. 2,5-Disubstituted 1,3,4-oxadiazoles have been synthesized by oxidation of 1-aroyl-2-arylidene hydrazines with potassium permanganate on the surface of a solid mineral support as well as in mixtures of acetone and water under microwave irradiation.
Experimental and Theoretical Studies on the Mechanism of DDQ-Mediated Oxidative Cyclization of N-Aroylhydrazones
Baek, Jihye,Je, Eun-Kyung,Kim, Jina,Qi, Ai,Ahn, Kwang-Hyun,Kim, Yongho
, p. 9727 - 9736 (2020/10/02)
The controversial single-electron-transfer process, frequently proposed in many 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)-mediated reactions, was investigated experimentally and theoretically using the oxidative cyclization of aroylhydrazone with DDQ. DDQ-mediated oxadiazole formation involves several processes, including cyclization to form an oxadiazole ring and N-H bond cleavage, either by proton, hydride, or hydrogen atom transfer. The detailed mechanistic study using the M06-2X density functional theory, and the 6-31+G(d,p) basis set, suggests that the pathways involving radical ion pair (RIP) intermediates, which resulted from single-electron transfer (SET), were found to be energetically nearly identical to the pathway without the SET. The substituent-dependent reactivity of oxadiazole formation was consistent with the free energy profiles of both pathways, with or without the SET. This result indicates that in addition to the electron-transfer pathway, the nucleophilic addition/elimination pathway for DDQ should be considered as a possible mechanism of the oxidative transformation reaction using DDQ.
Catalytic application of electrochemically prepared nickel oxide nanoparticles to synthesize 2, 5–disubstituted-1,3,4–oxadiazoles
Dare, Sushama B.,Gaikwad, Suresh T.,Rajbhoj, Anjali S.,Sawant, Manisha R.
, p. 300 - 308 (2020/07/03)
The present work aims to synthesize 2,5–disubstituted-1,3,4–oxadiazoles using electrochemically prepared nanoparticles of nickel oxide as catalyst.The nanoparticles thus prepared using electrochemical syntheses are in appreciable yield.The tetrabutyl phosphonium bromide has been used for capping followed by UV, FTIR, XRD, SEM EDS andTEM SAED studies for the characterization. The 2,5-disubstituted-1,3,4-oxadiazoles were synthesized from substituted benzoic acids and their hydrazides in microwave synthesis system using prepared nanoparticles as a catalyst.
2,5-Diaryloxadiazoles and their precursors as novel inhibitors of cathepsins B, H and L
Garg, Shweta,Raghav, Neera
, p. 64 - 74 (2016/07/06)
High levels of cathepsins indicated in various pathological conditions like arthritis, cancer progressions, and atherosclerosis explains the need to explore potential inhibitors of these proteases which can be of great therapeutic significance. We, in the present work, report the synthesis of some 2,5-diaryloxadiazoles from N-subsitutedbenzylidenebenzohydrazides. The synthesized compounds were screened for their inhibitory potential on cathepsins B, H and L. Structure Activity Relationship studies show that 2,5-diaryloxadiazoles were less inhibitory than their precursors. 1i and 2k have been found to be most inhibitory to cathepsins B and L. Their Ki values have been calculated as 11.38 × 10-8 M and 66.4 × 10-8 M for cathepsin B and 4.2 × 10-9 M and 47.31 × 10-9 M for cathepsin L, respectively. However, cathepsin H activity was maximally inhibited by compounds, 1e and 2c with Ki values of 4.4 × 10-7 M and 5.6 × 10-7 M, respectively. Enzyme kinetic studies suggest that these compounds are competitive inhibitors to the enzymes. The results have been compared with docking results obtained using iGemDock.
Study on DDQ-promoted synthesis of 2, 5-disubstituted 1, 3, 4-oxadiazoles from acid hydrazides and aldehydes
Jasiak, Karolina,Kudelko, Agnieszka,Zieliński, Wojciech,Ku?nik, Nikodem
, p. 87 - 106 (2017/02/23)
A facile stepwise synthesis of 2, 5-disubstituted 1, 3, 4-oxadiazoles proceeding via oxidative cyclization of N-acylhydrazones is reported. The reaction is efficiently promoted by 2, 3-dichloro-5, 6-dicyano-1, 4- benzoquinone (DDQ) to afford the desired products mostly in high yields and in relatively short times. The final 1, 3, 4-oxadiazole derivatives are also synthesized directly from acid hydrazides and aldehydes in a one-pot procedure. The substrate scope and limitations of the reported transformation are discussed in detail.
Ligand-free copper(0) catalyzed direct C-H arylation of 1,2,4-triazoles and 1,3,4-oxadiazoles with aryl iodides in PEG-400
Tadikonda, Ramu,Nakka, Mangarao,Rayavarapu, Srinuvasarao,Kalidindi, Siva Prasada Kumar,Vidavalur, Siddaiah
supporting information, p. 690 - 692 (2015/01/30)
A ligand-free copper catalyzed approach has been developed to the synthesis of 3,4,5-triaryl-1,2,4-triazoles and 2,5-diaryl-1,3,4-oxadiazoles by the direct arylation of corresponding 3,4-diaryl-1,2,4-triazoles and 2-aryl-1,3,4-oxadiazoles with aryl iodides using PEG-400 as reaction medium. The procedure is experimentally simple and free from addition of external chelating ligands or co-catalysts.
Palladium-Catalyzed Aminocarbonylation Reaction to Access 1,3,4-Oxadiazoles using Chloroform as the Carbon Monoxide Source
Li, Zhengyi,Wang, Liang
, p. 3469 - 3473 (2016/01/25)
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.
