37056-74-9Relevant articles and documents
Nitrone synthesis via pair electrochemical coupling of Nitro-Compounds with Benzyl Alcohol Derivatives
Salehzadeh, Hamid,Mashhadizadeh, Mohammad Hossein
, p. 9307 - 9312 (2019/07/08)
Here we report a paired electrochemical coupling of readily accessible nitro-compounds with benzyl alcohols to yield nitrone derivatives. In this work, electrochemical behavior of nitrobenzene and benzyl alcohol derivatives was studied by cyclic voltammetry and controlled potential coulommetry. Electrochemical reactions have been performed in aqueous/ethanol (or acetonitrile) solutions by employing common graphite electrodes and a simple controlled current protocol which can make this strategy more appealing than other conventional pathways.
Coupling of N -Nosylhydrazones with Nitrosoarenes: Transition-Metal-Free Approach to (Z)- N -Arylnitrones
Liu, Tingting,Liu, Zhaohong,Liu, Zhenhua,Hu, Donghua,Wang, Yeming
, p. 1728 - 1736 (2018/02/14)
An efficient and transition-metal-free protocol for the synthesis of (Z)- N -arylnitrones from the direct coupling of N -nosylhydrazones with nitrosoarenes under mild conditions is described. The protocol is compatible with a wide range of functional groups placed on both the reagents and provided the corresponding nitrones in good to excellent yields by simple recrystallization process. The use of these 1,3-dipoles for the synthesis of substituted indoles is elaborated for 2,3-diphenyl-1 H -indole.
One-pot synthesis of nitrones from nitro compounds by in situ trapping of arylhydroxylamines
Kazemi, Foad,Ramdar, Moosa,Tavana, Bahram,Davarpanah, Jamal
, p. 1101 - 1107 (2017/05/10)
Abstract: Highly efficient, convenient, simple procedure and a highly chemoselective method has been described for the conversion of nitroarenes to their corresponding nitrone derivatives by employing SnCl2·2H2O and Na2CO3 in the grinding apparatus in solvent-free conditions. Biaryl nitrones can be achieved via the condensation of an aldehyde with an unstable arylhydroxylamine which is prepared in situ through the reduction of the corresponding nitro aromatic compound. Interestingly, the slow and nonselective reduction of nitroarene to arylhydroxylamine step was directed with the condensation of in situ-prepared arylhydroxylamine with aromatic aldehyde (second step). Moreover, this protocol was successfully used for preparation of valuable dinitrones from dialdehyde and nitro aromatic compounds. For dinitrone preparation, dialdehyde compounds were first synthesized by the reaction of salicylaldehyde and glycol derivatives. Then, dialdehydes were reacted with reduced nitro compounds in optimal conditions that we used for synthesis of biaryl nitrones. Graphical Abstract: [Figure not available: see fulltext.].
Influence of the side-group at C=N bridging bond of bis-aryl Schiff bases on the wavelength of absorption maximum of ultraviolet absorption spectra
Luo, Qingqing,Cao, Chao-Tun,Cao, Zhongzhong,Cao, Chenzhong
, p. 406 - 413 (2016/07/28)
The compounds N-(benzylidene)-anilines XArCH=NArY (XBAY), N-(phenyl-ethylene)-anilines XArC(CH3)=NArY (XPEAY) and N-phenyl-α-phenylnitrones XArCH=N(O)ArY (XPNY) have bridging group CH=N, C(CH3)=N and CH=N(O) respectively, in which the C(CH3)=N has a side-group methyl CH3 at carbon end and the CH=N(O) has a side-group O atom at nitrogen end. In this work, a series of XPEAY and XPNY were synthesized, and their longest wavelength maximum λmax (nm) of ultraviolet absorption spectra were measured. Then the change regularity of the νmax (cm-1, νmax=1/λmax) of XPEAY and XPNY were investigated, and they were compared with that of XBAY (reported by ref.26). The results indicate: (1) There are no good linear relationships between the νmax of XBAYs and XPEAYs or XPNYs. (2) In case of a same set of X-Y group couples, the distribution of λmax of XPEAYs is larger than that of XPNYs. (3) The side-group CH3 makes the effect of σ(X) larger than that of σ(Y) on the νmax of XPEAYs, whereas the O atom makes the effect of σ(Y) larger than that of σ(X) on the νmax of XPNYs. (4) The cross-interaction between X and Y has important effect on the all νmax. However, the cross-interaction between CH3 and X/Y has not important effect on the νmax of XPEAY, and the cross-interaction between O and X/Y has not important effect on the νmax of XPNY. Copyright
Synthesis and evaluation of novel 4-[(3H,3aH,6aH)-3-phenyl)-4,6-dioxo-2- phenyldihydro-2H-pyrrolo[3,4-d]isoxazol-5(3H,6H,6aH)-yl]benzoic acid derivatives as potent acetylcholinesterase inhibitors and anti-amnestic agents
Anand, Preet,Singh, Baldev
, p. 521 - 530 (2012/03/09)
The present study was designed to synthesize and evaluate pyrrolo-isoxazole benzoic acid derivatives as potential acetylcholinesterase (AChE) inhibitors for the management of Alzheimer's disease. The synthesis of pyrrolo-isoxazole benzoic acid derivatives involved ring opening cyclization of p-aminobenzoic acid with maleic anhydride to yield maleanilic acid, which in turn afforded N-arylmaleimide via ring closed cyclization. Azomethine-N-oxides were obtained by condensation of N-arylhydroxylamine with differently substituted benzaldehydes followed by refluxing of N-arylmaleimide with differently substituted azomethine-N-oxides to pyrrolo-isoxazole benzoic acid derivatives as cis- and trans-stereoisomers. The synthesized compounds were evaluated in vitro for AChE inhibitory activity in rat brain homogenate with donepezil as standard AChE inhibitor. Thereafter, the most potent test compound was evaluated for in vitro butyrylcholinesterase inhibitory activity and in vivo memory evaluation in scopolamine (0.4 mg/kg)-induced amnesia in mice by employing Morris water maze test. All pyrrolo-isoxazole benzoic acid derivatives demonstrated potent AChE inhibitory activity. Most of compounds exhibited similar activity to donepezil and four of them (7h, 7i, 8i, and 8h, IC50 = 19.1 ± 1.9-17.5 ± 1.5 nM) displayed higher inhibitory activity as compared to donepezil (21.5 ± 3.2 nM) with compound 8ia (IC50 = 17.5 ± 1.5 nM) being the most active one. The test compound 8ia also ameliorated scopolamine-induced amnesia in mice in terms of restoration of time spent in target quadrant (TSTQ) and escape latency time (ELT). It may be concluded that pyrrolo-isoxazole benzoic acid derivatives may be employed as potential AChE inhibitors.
Synthesis and biological potential of nitrones of 4-chlorobenzaldehyde and ethylvanillin
Manrao,Matharu, Balbir Kaur,Gill,Kaul,Sharma
experimental part, p. 531 - 534 (2010/07/15)
Nitrones of 4-chiorobenzaldehyde (1a-6a) and ethylvanillin (1b-6b) were synthesized by condensing 4-chlorobenzaldehyde (a) and ethylvanillin (b) with phenylhydroxylamines (1-6) in equimolar ratio. The synthesized nitrones were characterized on the basis of elemental analysis and spectral studies and screened for antifungal potential against six phytopathogenic fungi and nematicidal activity against two nematodes.
Exploiting microwave-assisted neat procedures: synthesis of N-aryl and N-alkylnitrones and their cycloaddition en route for isoxazolidines
Andrade, Marta M.,Barros, Maria Teresa,Pinto, Rui C.
, p. 10521 - 10530 (2008/12/23)
Microwave irradiation allows increasing the speed of several reactions and also offers the possibility of eliminating poisoning organic solvents. In this work we report the microwave-assisted neat synthesis of α-phenyl-tert-butylnitrone (PBN) and other alkyl and aryl nitrones and also the rapid synthesis of isoxazolidines resulting from 1,3-dipolar cycloaddition of nitrones to ethyl trans-crotonate.
Synthesis of C, N-diaryl nitrones from the reduction of nitroarene with aromatic aldehydes promoted by metallic samarium
Jia, Xueshun,Li, Dafeng,Huang, Qing,Zhu, Li,Li, Jian
, p. 308 - 309 (2008/02/08)
A mild and facile reduction of nitroarene with aromatic aldehydes promoted by metallic samarium to C, N-diaryl nitrones in moderate yields has been developed.
