626-43-7Relevant academic research and scientific papers
Determination and identification of metabolites of the fungicides Iprodione and Procymidone in compost
Vanni, Adriano,Gamberini, Roberta,Calabria, Adelaide,Nappi, Pina
, p. 1431 - 1439 (2000)
The main metabolites formed from Iprodione and Procymidone during the composting process have been isolated and identified by HPLC-DAD-MSD. After addition of the fungicides to the composting pile, we monitored the reaction of the two analytes and the form
Chemical and Biological Transformation of the Fungicide Vinclozolin
Mercadier, Christine,Vega, Danielle,Bastide, Jean
, p. 3817 - 3822 (1998)
Two mixed bacterial cultures were isolated from a French soil adapted to the dicarboximide fungicide vinclozolin. The vinclozolin was transformed by the mixed bacterial cultures according to two degradation pathways: (a) the formation of 2-[[(3,5-dichlorophenyl)carbamoyl]oxy]-2-methyl-3-butenoic acid and then 3,5-dichloroaniline or (b) the formation of 3′,5′-dichloro-2-hydroxy-2-methylbut-3-enanilide and then 3,5-dichloroaniline. The structure of 2-[[(3,5-dichlorophenyl)-carbamoyl]oxy]-2-methyl-3-butenoic acid was unambiguously established by 1H and 13C 2-D NMR analysis. A bacterial strain isolated from soil that degrades this compound was identified as a strain of Corynebacterium sp. Attempts to obtain pure vinclozolin-degrading strains via 3′,5′-dichloro-2-hydroxy-2-methylbut-3-enanilide were unsuccessful.
Cyclic (Alkyl)(amino)carbene Ligand-Promoted Nitro Deoxygenative Hydroboration with Chromium Catalysis: Scope, Mechanism, and Applications
Zhao, Lixing,Hu, Chenyang,Cong, Xuefeng,Deng, Gongda,Liu, Liu Leo,Luo, Meiming,Zeng, Xiaoming
supporting information, p. 1618 - 1629 (2021/01/25)
Transition metal catalysis that utilizes N-heterocyclic carbenes as noninnocent ligands in promoting transformations has not been well studied. We report here a cyclic (alkyl)(amino)carbene (CAAC) ligand-promoted nitro deoxygenative hydroboration with cost-effective chromium catalysis. Using 1 mol % of CAAC-Cr precatalyst, the addition of HBpin to nitro scaffolds leads to deoxygenation, allowing for the retention of various reducible functionalities and the compatibility of sensitive groups toward hydroboration, thereby providing a mild, chemoselective, and facile strategy to form anilines, as well as heteroaryl and aliphatic amine derivatives, with broad scope and particularly high turnover numbers (up to 1.8 × 106). Mechanistic studies, based on theoretical calculations, indicate that the CAAC ligand plays an important role in promoting polarity reversal of hydride of HBpin; it serves as an H-shuttle to facilitate deoxygenative hydroboration. The preparation of several commercially available pharmaceuticals by means of this strategy highlights its potential application in medicinal chemistry.
Mechanochemical synthesis of aromatic sulfonamides
Mkrtchyan, Satenik,Iaroshenko, Viktor O.
supporting information, p. 11029 - 11032 (2021/11/03)
A three-component Pd-catalysed aminosulfonylation reaction of K2S2O5 and amine with aryl bromides or aromatic carboxylic acids was developed. This strategy was developed to utilise mechanical energy and accommodate primary as well as secondary aliphatic and aromatic amines to provide a new shortcut to a wide range of sulfonamides. Studies on the scope and limitations of the reaction indicated its tolerance of a vast range of functional groups and many structural patterns. The reactions were scaled up to gram quantities.
High yielding electrophilic amination with lower order and?higher order organocuprates: Application of acetone O-(4-Chlorophenylsulfonyl)oxime in the construction of the C?N bond at room temperature
Duran, Serdar,Korkmaz, Adem
, p. 2077 - 2087 (2021/05/27)
Electrophilic amination reaction was performed with lower order and?higher order organocuprates using acetone O-(4-Chlorophenylsulfonyl)oxime (1). It was proceeded smoothly at room temperature in the presence of organocuprates to provide the corresponding primary amines in good yields with 10 and 60 min, respectively. The primary amine yields of the electrophilic amination of bromomagnesium organocyanocuprates and dibromomagnesium diorganocyanocuprates were obtained 52–72% and 58–83%, respectively. We observed that higher order organocuprates were more successful than lower order organocuprates in the synthesis of functionalized arylamines by electrophilic amination.
Room-temperature copper-catalyzed electrophilic amination of arylcadmium iodides with ketoximes
Korkmaz, Adem
, p. 3119 - 3125 (2021/05/10)
We started our study by preparation two ketoximes. Later, there were studies to reveal these ketoximes' effects in the electrophilic amination reaction with organocadmium reagents. Primarily, it was observed that arylcadmium iodides could not be reacted with ketoximes at room temperature in the absence of a catalyst. CuCN was a suitable catalyst for this electrophilic amination reaction of arylcadmium iodides and allowed the preparation of functionalized aniline derivatives in good yields under mild reaction conditions. We obtained the results indicated that the yield of primary arylamines was strongly dependent on the steric and electronic effects of organocadmium reagent and amination agent. In the case of both amination reagents, meta-substituted arylamines were obtained in higher yields than para-substituted arylamines. We observed that acetone O-(4-chlorophenylsulfonyl)oxime, 1, as an aminating agent, was more successful than acetone O-(2-Naphthylsulfonyl)oxime, 2, in the synthesis of functionalized arylamines by electrophilic amination of corresponding aryl cadmium iodides. In this method, there is no cadmium release to the environment.
Hydrogenation of nitroarenes to anilines in a flow reactor using polystyrene supported rhodium in a catalyst-cartridge (Cart-Rh@PS)
Sharma, Saurabh,Yamini,Das, Pralay
supporting information, p. 1764 - 1769 (2019/01/28)
The present methodology described the chemo-selective hydrogenation of various nitroarenes in a flow reactor under polystyrene supported rhodium in a catalyst-cartridge (Cart-Rh@PS) as a heterogeneous nano-catalyst. The polystyrene supported Rh (Rh@PS) nanoparticles (NPs) were prepared by following our earlier reported protocol and packed inside the catalyst-cartridge (Cat-Cart) to obtain Cart-Rh@PS, which is compatible with ThalesNano's H-Cube Pro flow system. The advantages of the prepacked catalyst Cart-Rh@PS are as follows: no need for catalyst activation up to 12 runs, negligible metal leaching detected by ICP-AES analysis and significantly less back pressure generated under the flow conditions. The same catalyst, Cart-Rh@PS, was also effective up to a 1 gram scale for the reduction of nitroarenes and reusable for successive runs. The hydrogenation in the flow reactor is a greener approach for the reduction of nitroarenes to their corresponding anilines in high yields.
meta-Nitration of Arenes Bearing ortho/para Directing Group(s) Using C?H Borylation
Li, Xuejing,Deng, Xingwang,Coyne, Anthony G.,Srinivasan, Rajavel
supporting information, p. 8018 - 8023 (2019/05/29)
Herein, we report the meta-nitration of arenes bearing ortho/para directing group(s) using the iridium-catalyzed C?H borylation reaction followed by a newly developed copper(II)-catalyzed transformation of the crude aryl pinacol boronate esters into the corresponding nitroarenes in a one-pot fashion. This protocol allows the synthesis of meta-nitrated arenes that are tedious to prepare or require multistep synthesis using the existing methods. The reaction tolerates a wide array of ortho/para-directing groups, such as ?F, ?Cl, ?Br, ?CH3, ?Et, ?iPr ?OCH3, and ?OCF3. It also provides regioselective access to the nitro derivatives of π-electron-deficient heterocycles, such as pyridine and quinoline derivatives. The application of this method is demonstrated in the late-stage modification of complex molecules and also in the gram-scale preparation of an intermediate en route to the FDA-approved drug Nilotinib. Finally, we have shown that the nitro product obtained by this strategy can also be directly converted to the aniline or hindered amine through Baran's amination protocol.
A 3, 5 - dichloroaniline synthetic method (by machine translation)
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Paragraph 0035-0050, (2017/07/19)
The invention discloses a 3, 5 - dichloroaniline synthetic method, in order to 1, 3, 5 - trichlorobenzene as raw materials, in the organic solvent, the addition of a base, ammonia solution or ammonium salt as the Ammon, the transition metal catalyst and under the action of the ligand, coupled reactions, to obtain the product 3, 5 - dichloroaniline. The method of the invention, and is simple, low cost, simple synthesis steps, only one step reaction can be by the 1, 3, 5 - trichlorobenzene direct coupling with ammonia to obtain the product 3, 5 - dichloroaniline, few by-products, three wastes, environmental protection, the updating process of the product, for reducing the 3, 5 - dichloroaniline and its synthesis of derivatives cost is of great significance. (by machine translation)
Glucose promoted facile reduction of azides to amines under aqueous alkaline conditions
Chandna, Nisha,Kaur, Fatehjeet,Kumar, Shobhna,Jain, Nidhi
supporting information, p. 4268 - 4271 (2017/09/29)
A quick and efficient method for the reduction of azides to amines in water using d-glucose and KOH as green reagents is reported. The protocol is simple, inexpensive, scalable, and can be applied to different aromatic, heteroaromatic and sulphonyl azides. A high level of chemoselectivity is observed for azide reduction in the presence of other reducible functionalities like cyano, nitro, ether, ketone, amide and acid. The reaction gets completed in a short time (5-20 minutes), and furnishes the amines in high yield (85-99%). Unlike conventional hydrogenations, this reduction protocol does not require any metal catalyst, elaborate experimental setup or use of high-pressure equipment.
