19865-60-2

Upstream product

• 104-88-1 4-chlorobenzaldehyde 
• 823-86-9 N-(4-chlorophenyl)hydroxylamine 
• 100-00-5 4-chlorobenzonitrile 
• 873-76-7 para-Chlorobenzyl alcohol 
• 932-98-9 1-chloro-4-nitroso-benzene 

Downstream Products

• 1028342-30-4 (3R,5R)-2,3-di(4-chlorophenyl)-5-ethoxyisoxazolidine 
• 1751-80-0 (E)-4-chloro-N-(4-chlorobenzylidene)benzenamine 

Relevant academic research and scientific papers

Nitrone synthesis via pair electrochemical coupling of Nitro-Compounds with Benzyl Alcohol Derivatives

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.

Metal-free approach for the ?-proline mediated synthesis of nitrones from nitrosobenzene

An efficient, and metal-free approach for the ?-proline mediated synthesis of nitrones from nitrosobenzene and benzaldehydes has been established. The reaction undergoes very efficiently at room temperature in methanol as a solvent. The reaction is assumed to involve that the initial formation of azomethine ylide and [2 + 3] cycloaddition of nitrosobenzene, followed by the subsequent retro [2 + 3] cycloaddition could offer the desired nitrone.

PVP-Pd nanoparticles as efficient catalyst for nitroarene reduction under mild conditions in aqueous media

The catalytic activity of PVP-Pd nanoparticles synthesized by electrochemical methods was explored in nitroaromatic hydrogenation reaction. In this transformation, the colloidal nanocatalyst proved to have outstanding catalytic activity under sustainable reaction conditions. This mild process efficiently reduced the nitroaromatic group at room temperature, without high pressure of molecular hydrogen and in aqueous medium. Furthermore, several functional groups were tolerated, given the corresponding substituted arylamines in excellent yields and with high TOF. In addition, one-pot reactions and tandem process were explored, in which nitroaromatic hydrogenation reaction was included in the synthesis of modified amines. This methodology was effectively incorporated in tandem reactions and one-pot procedures, achieving N-arylamines functionalized in good isolated yields. Finally, comparison of sustainable chemistry metrics analysis demonstrated that this methodology is a reliable approach to perform the nitro compound hydrogenation process.

Synthesis of Benzimidazolones via One-Pot Reaction of Hydroxylamines, Aldehydes, and Trimethylsilyl Cyanide Promoted by Diacetoxyiodobenzene

A novel and efficient PhI(OAc)2-promoted one-pot reaction of aromatic hydroxylamines, aldehydes, and TMSCN in the presence of BF3·Et2O is described. A wide variety of N-substituted benzimidazolones are obtained with satisfactory yields under mild reaction conditions. The method was proven to be efficient for the synthesis of benzimidazolone derivatives from readily available starting materials.

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

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 biological potential of nitrones of 4-chlorobenzaldehyde and ethylvanillin

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.

Enantioselective 1,3-dipolar cycloaddition of nitrones with ethyl vinyl ether: The difference between Bronsted and Lewis acid catalysis

(Chemical Equation Presented) Bronsted and Lewis face off: A new chiral N-triflyl phosphoramide is used for asymmetric 1,3-dipolar cycloaddition of diaryl nitrones to ethyl vinyl ether to give the endo products in up to 93% ee (see scheme; Tf = trifluoromethanesulfonyl; Ad = adamantyl). The structure of the chiral phosphoramide was confirmed by X-ray crystallographic analysis.

Synthesis of C, N-diaryl nitrones from the reduction of nitroarene with aromatic aldehydes promoted by metallic samarium

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.

1,3-Dipolar cycloadditions. Part-XIII: Microwave irradiation assisted synthesis and spectroscopic investigations of C-aryl-N-phenyl and C-aryl-N-(4′-chlorophenyl)nitrones

C-Aryl-N-phenylnitrones have been prepared in very high yields from N-phenylhydroxylamine and aryl aldehydes using the microwave irradiation technique within a few minutes. The synthesis of a new series of nitrones, viz. the series of C-aryl-N-(4′-chlorop

1,3-Dipolar cycloaddition reactions of nitrones to prop-1-ene-1,3-sultone

The reaction of prop-1-ene-1,3-sultone (1) with a variety of nitrones 2 afforded novel [3+2] cycloaddition products 3, 4, and 5 in good yield. Excellent regio- and stereoselectivity were achieved in the cycloaddition reaction with phenylnitrones.