35427-95-3

Upstream product

• 89-98-5 2-chloro-benzaldehyde 
• 100-65-2 N-Phenylhydroxylamine 
• 98-95-3 nitrobenzene 
• 586-96-9 Nitrosobenzene 

Downstream Products

• 32347-02-7 2-chlorobenzalaniline 
• 32979-96-7 meso-1,2-Di-o-chlorphenyl-N,N'-diphenylethylendiamin 
• 1123200-93-0 C₁₇H₁₇ClN₂O₃ 
• 1360631-50-0 3-(2-chlorophenyl)-2-phenyl-2,3-dihydrobenzo[d]isoxazole 
• 1254524-71-4 N-(1-(2-chlorophenyl)-2-phenylethyl)-N-phenyl-O-(trimethylsilyl)hydroxylamine 
• 1401091-99-3 C₂₂H₃₂ClNOSi 
• 312732-89-1 2,2'-((2-chlorophenyl)methylene)bis(5,5-dimethylcyclohexane-1,3-dione) 
• 79887-80-2 9-(2-chlorophenyl)-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-2H-xanthen-1,8-dione 
• 15851-88-4 5-(2-chlorobenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione 
• 96179-29-2 2-chlorophenyl-bis-(5-hydroxy-3-methyl-1-phenyl-4-pyrazolyl)methane 

Relevant academic research and scientific papers

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.

Coupling of N -Nosylhydrazones with Nitrosoarenes: Transition-Metal-Free Approach to (Z)- N -Arylnitrones

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.

Synthesis and Evaluation of Novel 5-cyclohexyl-2-(4″-substitutedphenyl)-3-(2″-substitutedphenyl)4H-2,3,3a,5,6,6a-hexahydropyrrolo[3,4-d]isoxazole-4,6-dione Derivatives for Their In Vitro Antioxidant and Antibacterial Activities

1,3-Dipolar cycloaddition reactions of N-cyclohexyl maleimide (1) with azomethine N-oxide (2) have afforded novel isoxazolidine (3) in excellent yield. Their structures have been characterized from their IR,1H-NMR,13C-NMR,1H,1H-COSY, MS(ESI), and elemental analysis techniques. In vitro antibacterial activity of the synthesized compounds were investigated against a representative panel of pathogenic strains specifically two Gram-positive bacteria (Staphylococcus aureus and Streptococcus pyogenes) and two Gram-negative bacteria (Pseudomonas aeruginosa and Escherichia coli) using agar-well diffusion assay. Some of the compounds (3a, 3k, 3n, and 3o) exhibited promising antibacterial activities. All the synthesized compounds have also been screened for their antioxidant activities and were found to be significantly active.

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.

Nickel(II)-Catalyzed Enantioselective 1,3-Dipolar Cycloaddition of Nitrones with α,β-Unsaturated Acylcarboxylates

The highly enantioselective 1,3-dipolar cycloaddition of nitrones with α,β-unsaturated acylcarboxylates was realized for the first time by using a chiral bis(indano-oxazoline)-based Ni complex. The reaction proceeded smoothly under mild conditions and provided isoxazolidines with three contiguous stereocenters in high yields with excellent diastereoselectivities (>20:1 dr) and enantioselectivities (up to 99 % ee). The reaction was scaled up to the gram scale, and the products were readily transformed into γ-amino alcohols and other potentially bioactive compounds.

Synthesis of Quinoline N-Oxides by Cobalt-Catalyzed Annulation of Arylnitrones and Alkynes

A new and straightforward protocol for the synthesis of quinoline N-oxides from the annulation of arylnitrones and alkynes is described. For the first time, a [4+2] cyclization of nitrone and alkynes has been achieved by cobalt catalysis via a nitrone-assisted dual C–H cleavage under relatively mild conditions. (Figure presented.).

Synthesis of 2,3-Disubstituted NH Indoles via Rhodium(III)-Catalyzed C-H Activation of Arylnitrones and Coupling with Diazo Compounds

A rhodium-catalyzed intermolecular coupling between arylnitrones and diazo compounds by C-H activation/[4 + 1] annulation with a C(N2)-C(acyl) bond cleavage is reported, and 2,3-disubstituted NH indoles are directly synthesized in up to a 94% yield. A variety of functional groups are applicable to this reaction to give the corresponding products with high selectivity. Compared to other previously reported Rh(III)-catalyzed synthesis of homologous series, this method is simpler, more general, and more efficient.

Iron-Catalyzed Cyclization of Nitrones with Geminal-Substituted Vinyl Acetates: A Direct [4 + 2] Assembly Strategy Leading to 2,4-Disubstituted Quinolines

An iron-catalyzed intermolecular [4 + 2] cyclization of arylnitrones with geminal-substituted vinyl acetates was developed for the synthesis of 2,4-disubstituted quinolines in moderate to good yields with good functional group compatibilities. Preliminary mechanistic studies suggest a plausible iron-catalyzed C-H activation process under external-oxidant-free conditions.

An unexpected catalytic synthesis of novel and known bis(pyrazolyl) methanes by the use of α-aryl-N-phenyl nitrones in aqueous media

Reaction of -aryl-N-phenyl nitrones with 3.methyl-1-phenyl-2-pyrazoline-5-one in the presence of a catalytic amount of silica tungstic acid in EtOH/H2O afforded, unexpectedly, high yields of bis(3-hydroxy-1-phenylpyrazolyl)-arylmethanes instead of the two possible 1,3-addition products. This is the first report of the synthesis of bis(3-hydroxy-1-phenylpyrazolyl)-arylmethanes via the reaction of nitrones and a pyrazolin-5-one. A possible mechanism for the process is suggested.

Synthesis and evaluation of novel 2,3,5-triaryl-4H,2,3,3a,5,6,6a- hexahydropyrrolo[3,4-d]isoxazole-4,6-diones for advanced glycation end product formation inhibitory activity

The synthesis of some biologically interesting pyrrolo-isoxazolidine derivatives was accomplished by the 1,3-dipolar cycloaddition reaction of substituted azomethine N-oxides 1 with substituted N-aryl maleimides 2 leading to the formation of new stereoisomeric 2,3,5-triaryl-4H,2,3,3a,5,6,6a- hexahydropyrrolo[3,4-d]isoxazole-4,6-dione derivatives 3 in excellent yields. The synthesized compounds have been screened for their advanced glycation end (AGE) product formation inhibitory activity on the basis of their ability to inhibit the formation of AGEs in the bovine serum albumin (BSA)-glucose assay. All the synthesized compounds have been found to exhibit significant activity against AGE formation.