19865-57-7

Usage

InChI:InChI=1/C13H10N2O3/c16-14(12-6-2-1-3-7-12)10-11-5-4-8-13(9-11)15(17)18/h1-10H

Upstream product

• 98-95-3 nitrobenzene 
• 99-61-6 3-nitro-benzaldehyde 
• 100-65-2 N-Phenylhydroxylamine 
• 619-25-0 3-Nitrobenzyl alcohol 
• 586-96-9 Nitrosobenzene 

Downstream Products

• 56803-26-0 N-acetyl-N-(3-nitro-benzoyl)-aniline 
• 19744-03-7 3-(3-nitro-phenyl)-2,5-diphenyl-isoxazolidine 
• 19874-62-5 3-(3-nitro-phenyl)-2,5,5-triphenyl-isoxazolidine 
• 29068-09-5 3-(3-nitro-phenyl)-2-phenyl-7a-pyrrolidin-1-yl-octahydro-benzo[d]isoxazole 
• 19744-07-1 5-acetoxy-3-(3-nitro-phenyl)-2-phenyl-isoxazolidine 
• 29348-00-3 5t,7t-dimethyl-3ξ-(3-nitro-phenyl)-2-phenyl-3a-pyrrolidin-1-yl-(3ar,7ac)-octahydro-benzo[d]isoxazole 
• 33948-93-5 3-nitrophenyl-(bis-3-indolyl)methane 
• 82613-20-5 3,3'-((3-nitrophenyl)methylene)bis(2-methyl-1H-indole) 
• 73662-69-8 3-(m-nitrophenyl)-2-phenyl-5-(tricyanovinyl)-Δ⁴-1,2,4-oxadiazoline 
• 79687-70-0 3-(3-Nitro-phenyl)-2-phenyl-tetrahydro-furo[3,4-d]isoxazol-4-one 
• 25110-52-5 3-nitro-N¹,N²-diphenylbenzamidine 
• 139174-33-7 2-phenyl-3-(3-nitrophenyl)-6-oxo-8,8-dimethyl-1-oxa-2,7-diazaspiro<4,4>-non-2-ene 
• 139174-33-7 2-phenyl-3-(3-nitrophenyl)-6-oxo-8,8-dimethyl-1-oxa-2,7-diazaspiro<4,4>-non-2-ene 
• 141357-01-9 5-(1,2-O-Isopropylidene-α-D-xylo-tetrofuranos-4-yl)-3-(3-nitrophenyl)-2-phenylisoxazolidine 

Relevant academic research and scientific papers

A green synthesis of nitrones in glycerol

Abstract: An eco-friendly and efficient synthesis of nitrones is presented by condensation of an equimolar amount of aldehydes and N-substituted hydroxylamine hydrochlorides in glycerol as a recyclable solvent-catalyst. This novel protocol provides rapid and mild access to a series of nitrone derivatives in good to excellent yields in the absence of catalyst and base. Graphic abstract: SYNOPSIS In this study, a base-free protocol by using glycerol as the solvent-catalyst was applied for an eco-friendly synthesis of nitrones from the condensation of aldehydes and N-substituted hydroxylaminehydrochlorides.[Figure not available: see fulltext.].

Catalytic Diastereo- and Enantioselective Synthesis of 2-Imidazolinones

Chiral cyclic ureas (2-imidazolinones) were prepared by the reaction of nitrones and isocyanoacetate esters using a multicatalytic system that combines a bifunctional Br?nsted base-squaramide organocatalyst and Ag+ as a Lewis acid. The reaction could be achieved with a range of nitrones derived from aryl- and cycloalkylaldehydes with moderate diastereo- and good enantioselectivity. A plausible mechanism involving an initial formal [3 + 3] cycloaddition of the nitrone and isocyanoacetate ester, followed by rearrangement to an aminoisocyanate and cyclization to the imidazolinone, is proposed.

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.

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.

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 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.

Copper(I)-catalyzed three component reaction of sulfonyl azide, alkyne, and nitrone cycloaddition/rearrangement cascades: A novel one-step synthesis of imidazolidin-4-ones

A novel one-pot azide-alkyne/ketenimine-nitrone cycloaddition sequence that is induced by copper(I) and allows the transformation of sulfonyl azides, alkynes, and nitrones to highly substituted imidazolidin-4-ones is described. The corresponding heterogeneous version utilizing Cu(I)-modified zeolites as recyclable heterogeneous catalysts shows marginally improved yield and diastereoselectivity.

Studies of multicomponent Kinugasa reactions in aqueous media

Micelle-promoted, copper-catalyzed multicomponent Kinugasa reactions were studied in aqueous media. Reactions were performed in a 'single pot' for a series of in situ generated C,N-diphenylnitrones with Cu(I) phenylacetylide providing β-lactams in yields of 45-85%. Substituents affect the reaction by either accelerating cycloaddition or minimizing side reactions.

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

Microwave mediated synthesis of spiro-(indoline-isoxazolidines): Mechanistic study and biological activity evaluation

Regioisomeric spiro-(indoline-isoxazolidines) have been synthesized in moderate yields by the cycloaddition reaction between ethyl (3-indolylidene) acetate and various substituted α,N-diphenylnitrones, using environmentally benign microwave technology. A