30924-55-1

Upstream product

• 98-95-3 nitrobenzene 
• 135-02-4 ortho-anisaldehyde 
• 586-96-9 Nitrosobenzene 
• 100-65-2 N-Phenylhydroxylamine 

Downstream Products

• 1357560-73-6 C₂₀H₁₉NO₆ 
• 1357560-85-0 C₂₀H₁₉NO₆ 

Relevant academic research and scientific papers

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.

Trifluoromethyl Vinyl Sulfide: A Building Block for the Synthesis of CF3S-Containing Isoxazolidines

Trifluoromethyl vinyl sulfide, a potential building block for pharmaceutically and agrochemically relevant products, is prepared and used for the first time in high-pressure-mediated 1,3-dipolar cycloaddition reactions with nitrones to synthesize (trifluoromethyl)sulfanyl isoxazolidines.

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.

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.

1,3-dipolar cycloaddition reactions leading to the synthesis of new 2,3,5-triaryl-4h,2,3,3a,5,6,6a-hexahydropyrrolo[3,4-d]isoxazole-4,6-diones

Cycloaddition of C,N-diphenylnitrones 1 to N-aryl maleimides 2 afforded two diastereomeric isoxazolidines with high selectivity. The structure and steric configuration of the adducts have been assigned on the basis of 1H NMR, 1H NMR COSY, 13C NMR and IR spectroscopy. The π-π stacking interactions between maleimide's and nitrone's aromatic rings during the 1,3-dipolar cycloaddition were assumed to control the exo-endo selectivity of the reaction. Thus, the exo-endo ratio depends upon the position of the substituent present on the C-phenyl ring of the C,N-diphenylnitrones.

Rhodium-catalyzed cyclization of diynes with nitrones: A formal [2+2+5] approach to bridged eight-membered heterocycles

N-aryl-substituted nitrones were employed as fiveatom coupling partners in the rhodium-catalyzed cyclization with diynes. In this reaction, the nitrone moiety served as a directing group for the catalytic C-H activation of the N-aryl ring. This formal [2+2+5] approach allows rapid access to bridged eight-membered heterocycles with broad substrate scope. The results of this study may provide new insight into the chemistry of nitrones and find applications in the synthesis of other heterocycles,.

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

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 evaluation of hexahydropyrrolo[3,4-d]isoxazole-4,6-diones as anti-stress agents

A series of 2,3-diphenyl-5-(naphthalen-1-yl)-4H-2,3,3a,5,6,6a- hexahydropyrrolo[3,4-d]isoxazole-4,6-dione derivatives were synthesized via 1,3-dipolar cycloaddition of azomethine N-oxides with N-(α-naphthyl) maleimide. The pyrrolo-isoxazole derivatives were assigned cis- and trans- configurations (3-A and 3-B) with respect to proton C3-H on azomethinic carbon on the basis of their 1H NMR. The reaction proceeds through cis- endo addition rule indicating the predominance of cis isomer. The cis- and trans- isomers of a prototype compound 3a i.e., compound 3a-A and compound 3a-B were evaluated for anti-stress activity in immobilization-induced acute stress. Compound 3a-A (5 and 10 mg/kg) and compound 3a-B (10 mg/kg) attenuated immobilization stress-induced behavioral alterations in Swiss albino mice suggesting that pyrrolo-isoxazole may serve as lead molecule for the development of anti-stress agents.

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

?-? Molecular Complexes with Nitrones: PartIV - Substituent Effect in the Complexation of Aryl Nitrones with Tetracyanoethylene and 1,4-Benzoquinones

Charge-transfer complexes of some substituted nitrones with tetracyanoethylene and 1,4-benzoquinones have been studied spectrophotometrically.The stoichiometry and apparent formation constants of the complexes have been determined.From the energies of the charge-transfer transitions, the ionization potentials of the donors have been obtained.