620-25-7

Usage

InChI:InChI=1/C7H9NO/c1-6-3-2-4-7(5-6)8-9/h2-5,8-9H,1H3

Upstream product

• 99-08-1 1-methyl-3-nitrobenzene 
• 70-18-8 GLUTATHIONE 
• 620-26-8 3-nitrosotoluene 
• 64-19-7 acetic acid 
• 108-44-1 1-amino-3-methylbenzene 
• 105-56-6 ethyl 2-cyanoacetate 
• 1062320-37-9 C₁₄H₁₂N₂O₃ 
• 109-77-3 malononitrile 
• 163188-49-6 N-m-tolyl-α-phenylstyrylacrylohydroxamic acid 

Downstream Products

• 19618-06-5 (E)-di-m-tolyl-diazene-N-oxide 
• 71297-97-7 N,N'-bis(3-methylphenyl)-diazene N-oxide 
• 588-04-5 3,3'-dimethylazobenzene 
• 80411-72-9 1-(3'-methylphenylazo)naphthalene 
• 620-26-8 3-nitrosotoluene 
• 95-81-8 2-chloro-5-methylaniline 
• 2835-96-3 4-amino-2-methylphenol 
• 29027-17-6 2-chloro-3-methylaniline 
• 6933-10-4 amino-5-bromo-2-toluene 
• 755737-33-8 N-nitroso-N-m-tolyl-hydroxylamine 
• 7149-75-9 3-methyl-4-chloroaniline 
• 136-90-3 4-methoxy-3-methylaniline 
• 19618-06-5 3,3'-dimethylazoxybenzene 
• 97339-81-6 benzaldehyde-(N-m-tolyl oxime ) 

Relevant academic research and scientific papers

Electrochemically Tuned Oxidative [4+2] Annulation and Dioxygenation of Olefins with Hydroxamic Acids

This work represents the first [4+2] annulation of hydroxamic acids with olefins for the synthesis of benzo[c][1,2]oxazines scaffold via anode-selective electrochemical oxidation. This protocol features mild conditions, is oxidant free, shows high regioselectivity and stereoselectivity, broad substrate scope of both alkenes and hydroxamic acids, and is compatible with terpenes, peptides, and steroids. Significantly, the dioxygenation of olefins employing hydroxamic acid is also successfully achieved by switching the anode material under the same reaction conditions. The study not only reveals a new reactivity of hydroxamic acids and its first application in electrosynthesis but also provides a successful example of anode material-tuned product selectivity.

Redox-Neutral Selenium-Catalysed Isomerisation of para-Hydroxamic Acids into para-Aminophenols

A selenium-catalysed para-hydroxylation of N-aryl-hydroxamic acids is reported. Mechanistically, the reaction comprises an N?O bond cleavage and consecutive selenium-induced [2,3]-rearrangement to deliver para-hydroxyaniline derivatives. The mechanism is studied through both 18O-crossover experiments as well as quantum chemical calculations. This redox-neutral transformation provides an unconventional synthetic approach to para-aminophenols.

Selective Photoinduced Reduction of Nitroarenes to N-Arylhydroxylamines

We report the selective photoinduced reduction of nitroarenes to N-arylhydroxylamines. The present methodology facilitates this transformation in the absence of catalyst or additives and uses only light and methylhydrazine. This noncatalytic photoinduced transformation proceeds with a broad scope, excellent functional-group tolerance, and high yields. The potential of this protocol reflects on the selective and straightforward conversion of two general antibiotics, azomycin and chloramphenicol, to the bioactive hydroxylamine species.

Tandem selective reduction of nitroarenes catalyzed by palladium nanoclusters

We report a catalytic tandem reduction of nitroarenes by sodium borohydride (NaBH4) in aqueous solution under ambient conditions, which can selectively produce five categories of nitrogen-containing compounds: anilines, N-aryl hydroxylamines, azoxy-, azo- and hydrazo-compounds. The catalyst is in situ-generated ultrasmall palladium nanoclusters (Pd NCs, diameter of 1.3 ± 0.3 nm) from the reduction of Pd(OAc)2 by NaBH4. These highly active Pd NCs are stabilized by surface-coordinated nitroarenes, which inhibit the further growth and aggregation of Pd NCs. By controlling the concentration of Pd(OAc)2 (0.1-0.5 mol% of nitroarene) and NaBH4, the water/ethanol solvent ratio and the tandem reaction sequence, each of the five categories of N-containing compounds can be obtained with excellent yields (up to 98%) in less than 30 min at room temperature. This tunable catalytic tandem reaction works efficiently with a broad range of nitroarene substrates and offers a green and sustainable method for the rapid and large-scale production of valuable N-containing chemicals.

Synthesis of sulpha drug based hydroxytriazene derivatives: Anti-diabetic, antioxidant, anti-inflammatory activity and their molecular docking studies

Herein, we report synthesis, characterization, anti-diabetic, anti-inflammatory and anti-oxidant activities of hydroxytriazenes derived from sulpha drugs, namely sulphanilamide, sulphadiazine, sulphapyridine and sulphamethazine. Before biological screening of the compounds, theoretical prediction using PASS was done which indicates probable activities ranging from Pa (probable activity) values 65–98% for anti-inflammatory activity. As per the predication, experimental validation of some of the predicted activities particularly anti-diabetic, anti-inflammatory and anti-oxidant was done. Anti-diabetic activities have been screened using two methods namely α-amylase and α-glucosidase inhibition method and IC50 values were ranging from 66 to 260 and 148 to 401 μg/mL, while for standard drug acarbose the values were 12 μg/mL and 70 μg/mL, respectively. Docking studies have also been done for antidiabetic target pancreatic alpha amylase. The molecular docking studies in α-amylase enzyme reveal that the middle phenyl ring of all the compounds mainly occupies in the small hydrophobic pocket formed by the Ala198, Trp58, Leu162, Leu165 and Ile235 residues and sulphonamide moiety establish H-bond interaction by two water molecules. Further, anti-inflammatory activity has been evaluated using carrageenan induced paw-edema method and results indicate excellent anti-inflammatory activity by hydroxytriazenes (71 to 97%) and standard drug diclofenac 94% after 4 h of treatment. Moreover, antioxidant effect of the compounds was tested using DPPH and ABTS methods. All the compounds displayed good results (24–488 μg/mL) against ABTS radical and many compounds are more active than ascorbic acid (69 μg/mL) while all other compounds showed moderate activity against DPPH radical (292–774 μg/mL) and ascorbic acid (29 μg/mL). Thus, the studies reveal potential of sulfa drug based hydroxytriazenes as candidates for antidiabetic, anti-inflammatory and antioxidant activities which have been experimentally validated.

A general and scalable synthesis of polysubstituted indoles

A consecutive 2-step synthesis of N-unprotected polysubstituted indoles bearing an electron-withdrawing group at the C-3 position from readily available nitroarenes is reported. The protocol is based on the [3,3]-sigmatropic rearrangement of N-oxyenamines generated by the DABCO-catalyzed reaction of N-arylhydroxylamines and conjugated terminal alkynes, and delivers indoles endowed with a wide array of substitution patterns and topologies.

Regioselective installation of fluorosulfate (-OSO2F) functionality into aromatic C(sp2)-H bonds for the construction of: Para-amino-arylfluorosulfates

The construction of para-amino-arylfluorosulfates was achieved through installation of fluorosulfate (-OSO2F) functionality into aromatic C(sp2)-H bonds by the reaction of N-arylhydroxylamine with sulfuryl fluoride (SO2Fs

Cobalt-Catalyzed Electrophilic Amination of Aryl- and Heteroarylzinc Pivalates with N-Hydroxylamine Benzoates

Aryl- and heteroarylzinc pivalates can be aminated with O-benzoylhydroxylamines at 25 °C within 2–4 h in the presence of 2.5–5.0 % CoCl2?2 LiCl to furnish the corresponding tertiary arylated or heteroarylated amines in good yields. This electrophilic amination also provides access to diarylamines and aryl(heteroaryl)amines. A new tuberculosis drug candidate (Q203) was prepared in six steps and 56 % overall yield by using this cobalt-catalyzed amination as the key step.

Synthesis of N-aryl and N-heteroaryl hydroxylamines via partial reduction of nitroarenes with soluble nanoparticle catalysts

Polystyrene-supported ruthenium nanoparticles enable the selective hydrazine-mediated reduction of nitroarenes to hydroxylamine products in high yield and selectivity. Key to obtaining the hydroxylamine product in good yield was the use of organic solvents capable of solubilizing the polystyrene-supported nanoparticle catalyst. N-aryl and N-heteroaryl hydroxylamines are generated under exceptionally mild conditions and in the presence of a various easily reduced functional groups.

Hydroxamic Acids as Chemoselective (ortho-Amino)arylation Reagents via Sigmatropic Rearrangement

The use of readily available hydroxamic acids as reagents for the chemoselective (ortho-amino)arylation of amides is described. This reaction proceeds under metal-free, mild conditions, displays a very broad scope, and constitutes a direct approach for the metal-free attachment of aniline residues to carbonyl derivatives.