611-22-3Relevant academic research and scientific papers
Kinetics and mechanism of the mineral acid catalysed reactions of hydroxamic acids
Ghosh, Kallol K.,Vaidya, Jyoti,Sinha, Daliya
, p. 563 - 573 (2004)
There is currently a great deal of interest in the chemistry of hydroxamic acids. In recent years we have been studying the synthesis, structure and nucleophilicities of hydroxamic acids. This paper reports a kinetic study of reactivity of some hydroxamic acids RC(O)·N(OH)R′; R = C 6H5·CH=CH, R′ = 4-CH3· C6H4 [p-tolylcinnamo hydroxamic acid]; R = C 6H5, R′ 4-CH3·C6H 4 [p-tolylbenzo hydroxamic acid]; R = C6H5, R′ = 2-CH3·C6H4 [o-tolylbenzo hydroxamic acid] in aqueous mineral acids (HCl, HClO4 and H 2SO4). The rate data of hydrolysis reaction revealed that the reactivity/stability sequence of the compounds is generally p-TBHA > o-TBHA > p-TCHA. An excess acidity analysis reveals that the reaction proceeds by nucleophilic attack of water molecule on the protonated substrate.
Promoting effect of ethanol on the synthesis of N-(2-methylphenyl) hydroxylamine from o-nitrotoluene in Zn/H2O/CO2 system
Liu, Shi Juan,Wang, Yan Hua,Hao, Yuan Ping,Jiang, Jing Yang
, p. 221 - 224 (2011)
The promoting effect of ethanol on the synthesis of N-(2-methylphenyl) hydroxylamine from o-nitrotoluene in Zn/H2O/CO2 system was observed. By adding appropriate amount of ethanol, the selectivity of N-(2-methylphenyl)hydroxylamine increased from 71% to 90% when the reduction was carried out at 25 °C under normal pressure of CO2.
Bactericidal composition containing isotianil and osthole
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Paragraph 0019; 0029; 0034, (2021/08/11)
The invention discloses a bactericidal composition containing isotianil and osthole, and belongs to the technical field of pesticide preparation. The bactericidal composition comprises, by weight, 1-50% of isotianil, 0.1-10% of osthole, 5-10% of a bacteri
Tandem selective reduction of nitroarenes catalyzed by palladium nanoclusters
Yan, Ziqiang,Xie, Xiaoyu,Song, Qun,Ma, Fulei,Sui, Xinyu,Huo, Ziyu,Ma, Mingming
supporting information, p. 1301 - 1307 (2020/03/11)
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
Baroliya, Prabhat K.,Chauhan, R. S.,Dayma, Varsha,Dwivedi, Aparna,Goswami, A. K.,Sharma, Poonam,Tripathi, I. P.,Vanangamudi, Murugesan
, (2020/02/15)
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.
Synthesis of meta-substituted anilines via copper-catalyzed [1,3]-methoxy rearrangement
Ishida, Yasuhiro,Nakamura, Itaru,Tashiro, Hiroki,Terada, Masahiro
supporting information, p. 3794 - 3798 (2020/06/08)
meta-Substituted anilines were efficiently synthesized via copper-catalyzed [1,3]-methoxy rearrangement of N-methoxyanilines followed by Michael addition of nucleophiles to the in situ generated ortho-quinol imine. The present reaction exhibits excellent
A general and scalable synthesis of polysubstituted indoles
Diana-Rivero, Raquel,García-Tellado, Fernando,Tejedor, David
, (2021/06/14)
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.
Highly Selective and Solvent-Dependent Reduction of Nitrobenzene to N-Phenylhydroxylamine, Azoxybenzene, and Aniline Catalyzed by Phosphino-Modified Polymer Immobilized Ionic Liquid-Stabilized AuNPs
Doherty, Simon,Knight, Julian G.,Backhouse, Tom,Summers, Ryan J.,Abood, Einas,Simpson, William,Paget, William,Bourne, Richard A.,Chamberlain, Thomas W.,Stones, Rebecca,Lovelock, Kevin R. J.,Seymour, Jake M.,Isaacs, Mark A.,Hardacre, Christopher,Daly, Helen,Rees, Nicholas H.
, p. 4777 - 4791 (2019/05/17)
Gold nanoparticles stabilized by phosphine-decorated polymer immobilized ionic liquids (AuNP@PPh2-PIILP) is an extremely efficient multiproduct selective catalyst for the sodium borohydride-mediated reduction of nitrobenzene giving N-phenylhydroxylamine, azoxybenzene, or aniline as the sole product under mild conditions and a very low catalyst loading. The use of a single nanoparticle-based catalyst for the partial and complete reduction of nitroarenes to afford three different products with exceptionally high selectivities is unprecedented. Under optimum conditions, thermodynamically unfavorable N-phenylhydroxylamine can be obtained as the sole product in near quantitative yield in water, whereas a change in reaction solvent to ethanol results in a dramatic switch in selectivity to afford azoxybenzene. The key to obtaining such a high selectivity for N-phenylhydroxylamine is the use of a nitrogen atmosphere at room temperature as reactions conducted under an inert atmosphere occur via the direct pathway and are essentially irreversible, while reactions in air afford significant amounts of azoxy-based products by virtue of competing condensation due to reversible formation of N-phenylhydroxylamine. Ultimately, aniline can also be obtained quantitatively and selectively by adjusting the reaction temperature and time accordingly. Introduction of PEG onto the polyionic liquid resulted in a dramatic improvement in catalyst efficiency such that N-phenylhydroxylamine could be obtained with a turnover number (TON) of 100000 (turnover frequency (TOF) of 73000 h-1, with >99% selectivity), azoxybenzene with a TON of 55000 (TOF of 37000 h-1 with 100% selectivity), and aniline with a TON of 500000 (TOF of 62500 h-1, with 100% selectivity). As the combination of ionic liquid and phosphine is required to achieve high activity and selectivity, further studies are currently underway to explore whether interfacial electronic effects influence adsorption and thereby selectivity and whether channeling of the substrate by the electrostatic potential around the AuNPs is responsible for the high activity. This is the first report of a AuNP-based system that can selectively reduce nitroarenes to either of two synthetically important intermediates as well as aniline and, in this regard, is an exciting discovery that will form the basis to develop a continuous flow process enabling facile scale-up.
Regioselective installation of fluorosulfate (-OSO2F) functionality into aromatic C(sp2)-H bonds for the construction of: Para-amino-arylfluorosulfates
Fang, Wan-Yin,Zha, Gao-Feng,Zhao, Chuang,Qin, Hua-Li
supporting information, p. 6273 - 6276 (2019/06/07)
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
A O-methyl phenyl hydroxylamine production method (by machine translation)
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Paragraph 0029; 0030; 0031; 0032; 0033; 0034, (2017/08/25)
The invention discloses a method for the production of ortho-methyl phenyl hydroxylamine method, steps are as follows: the O-nitro-toluene, solvent and catalyst into reactor, stirring, O-nitro-toluene, solvent and catalyst weight ratio of 35 - 45:80 - 150
