1467-70-5Relevant articles and documents
Synthesis of aryl α-keto-acids via the Cu-catalyzed conversion of aryl nitroaldol products
Nikalje, Milind D.,Ali, Iliyas Sayyed,Dewkar, Gajanan K.,Sudalai
, p. 959 - 961 (2000)
Cu(II) salts efficiently catalyze the conversion of a variety of aryl nitroaldol products to afford the corresponding aryl α-keto-acids in high yields using 30% aq. AcOH:MeOH (1:1) as the solvent. (C) 2000 Elsevier Science Ltd.
Synthesis of α-Keto Acids via Oxidation of Alkenes Catalyzed by a Bifunctional Iron Nanocomposite
Song, Tao,Ma, Zhiming,Wang, Xiaoxue,Yang, Yong
supporting information, p. 5917 - 5921 (2021/07/31)
An efficient methodology for synthesis of α-keto acids via oxidation of alkenes using TBHP as oxidant catalyzed by a bifunctional iron nanocomposite has been established. A variety of alkenes with different functional groups were smoothly oxidized into their corresponding α-keto acids in up to 80% yield. Moreover, the bifunctional iron nanocomposite catalyst showed outstanding catalytic stability for successive recycles without appreciable loss of activity.
Novel peptidomimetic peptide deformylase (PDF) inhibitors of Mycobacterium tuberculosis
Gokhale, Kunal M.,Telvekar, Vikas N.
, p. 148 - 156 (2020/08/26)
Emergence of MDR-TB and XDR-TB led to the failure of available anti-tubercular drugs. In order to explore, identify and develop new anti-tubercular drugs, novel peptidomimetic series of Mtb–peptide deformylase (PDF) inhibitors was designed and synthesized. In vitro antimycobacterial potential of compounds was established by screening of compounds against Mycobacterium tuberculosis H37Rv strain using MABA. Among them, ester series of compounds 4a, 4b, 4c, 4d, and 4e were found most active, with compound 4c being highly active and exhibiting minimum inhibitory concentration of 6.25?μg/ml against M.?tb H37Rv strain. Additionally, the compounds were docked to determine the probable binding interactions and understand the mechanism of action of most active molecules on Mtb-peptide deformylase (PDF), which is involved in the mycobacterium protein synthesis.
Possible competitive modes of decarboxylation in the annulation reactions ofortho-substituted anilines and arylglyoxylates
Laha, Joydev K.,Panday, Surabhi,Tomar, Monika,Patel, Ketul V.
supporting information, p. 845 - 853 (2021/02/09)
Annulation reactions ofortho-substituted anilines and arylglyoxylates in the presence of K2S2O8at 80 °C under metal-free neutral conditions have been investigated, which extended a platform for the tandem synthesis of nitrogen heterocycles. While arylglyoxylic acids are known to undergo decarboxylation to form an acyl radical in the presence of K2S2O8and used in the Minisci acylation of electron-deficient (hetero)aromatics, their reactions with electron-richortho-substituted anilines to form nitrogen heterocycles have recently been studied. Depending upon the experimental conditions used in the reactions, the mechanism of the formation of heterocycles involving reactions of an acyl radical or aryl iminocarboxylic acids has been postulated. Given the subtle understanding of the mechanisms of annulation reactions of 2-substituted anilines and arylglyoxylates in the presence of K2S2O8, an extensive mechanistic investigation was undertaken. In the current study, the various mechanistic pathways including the generation of acyl, imidoyl, aminal, and N,O-hemiketal radicals have been postulated based on different possible decarboxylation modes. Some of the proposed intermediates are supported based on the available analytical data. The protocol uses a single, inexpensive reagent K2S2O8, which offers not only transition-metal-free conditions but also serves as the reagent for the key decarboxylation step. Taken together, this study complements the current development of the annulation reactions of 2-substituted anilines and arylglyoxylates in terms of synthesis and mechanistic understanding.
Rapid assembly of α-ketoamides through a decarboxylative strategy of isocyanates with α-oxocarboxylic acids under mild conditions
Huang, Junjie,Liang, Baihui,Chen, Xiuwen,Liu, Yifu,Li, Yawen,Liang, Jingwen,Zhu, Weidong,Tang, Xiaodong,Li, Yibiao,Zhu, Zhongzhi
supporting information, p. 4783 - 4787 (2021/06/11)
A simple and practical method for α-ketoamide synthesis via a decarboxylative strategy of isocyanates with α-oxocarboxylic acids is described. The reaction proceeds at room temperature under mild conditions without an oxidant or an additive, showing good substrate scope and functional compatibility. Moreover, the applicability of this method was further demonstrated by the synthesis of various bioactive molecules and different application examples through a two-step one-pot operation.
K2S2O8mediated synthesis of 5-Aryldipyrromethanes and meso-substituted A4-Tetraarylporphyrins
Laha, Joydev K.,Hunjan, Mandeep Kaur
, p. 664 - 673 (2021/06/03)
The synthesis of dipyrromethanes from pyrrole and arylglyoxylic acids in the presence of K2S2O8at 90 C is reported affording dipyrromethanes in very good yields. Unlike an excess pyrrole traditionally used in dipyrromethane synthesis, the current method uses a stoichiometric amount of pyrrole avoiding any use of Br?nsted or Lewis acid. A gram scale synthesis of 5-phenyldipyrromethane is also achieved demonstrating potential scale up of dipyrromethanes using this method feasible. Subsequently, dipyrromethanes were converted to A4tetraarylporphyrins also in the presence of K2S2O8at 90C. A direct synthesis of A4-tetraphenylporphyrin from excess pyrrole and phenylglyoxylic acid in the presence of K2S2O8 at 90C is also reported.
Minisci aroylation of N-heterocycles using choline persulfate in water under mild conditions
Hunjan, Mandeep Kaur,Laha, Joydev K.,Tinwala, Ummehani
, p. 22853 - 22859 (2021/12/24)
Metal persulfate mediated thermal oxidative organic transformations invariably require a higher temperature and frequently use an organic solvent. The objective of this work was to develop persulfate mediated oxidative transformations that can be performed nearly at room temperature using water as a solvent. This report describes modified Minisci aroylation of isoquinolines with arylglyoxylic acids using choline persulfate and its pre-composition (choline acetate and K2S2O8) in water at 40 °C. A few other nitrogen heterocycles were also utilized affording various aroylated products in good to excellent yields. Unlike metal persulfate that could produce metal salt byproducts, a key feature of the chemistry reported herein includes the use of environmentally benign choline persulfate containing biodegradable choline as a counter-cation, the Minisci reaction demonstrated at 40 °C in water as the only solvent, and unconventional activation of persulfate. This journal is
Alpha-oxo-2-furyl acetic acid and preparation method of ester of alpha-oxo-2-furyl acetic acid
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Paragraph 0050-0052, (2021/05/01)
The invention belongs to the field of preparation of medical intermediates, and particularly relates to a preparation method of alpha-oxo-2-furyl acetic acid (furanone acid) and ester thereof. 2-ketosaccharic acid is used as a raw material, and in water, an organic solvent or an ionic liquid, alpha-oxo-2-furyl acetic acid and ester thereof are formed through acid catalytic dehydration. The preparation steps of the alpha-oxo-2-furyl acetic acid and the ester thereof are simple, the raw materials are cheap, and the operation is convenient. The serious problems of serious three-waste pollution such as more side reactions, NOx generation, high salt content of reaction wastewater and serious standard exceeding of COD in the traditional process of preparing alpha-oxo-2-furyl acetic acid and ester thereof by oxidizing acetylfuran are avoided.
Preparation method of [alpha]-oxo-2-furanacetic acid
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Paragraph 0032; 0035-0041; 0042; 0045-0049; 0050; 0053-005, (2021/05/01)
The invention belongs to the field of preparation of organic compounds, and particularly relates to a preparation method of [alpha]-oxo-2-furanacetic acid, which comprises the following steps: 1) preparing oxalic acid and an organic alkali solution, controlling the temperature to 5-10 DEG C, dropwisely adding a trichloromethyl carbonate solution into the oxalic acid and organic alkali solution, and keeping the temperature for 2-4 hours until the solid is completely dissolved to obtain a solution A; obtaining a first solution; 2) preparing a furan and Lewis acid solution, controlling the temperature to be 20-25 DEG C, then dropwise adding the first solution into the furan and Lewis acid solution, and carrying out heat preservation for 1-2 hours to obtain a second solution; and 3) quenching the second solution at 0-10 DEG C to obtain the [alpha]-oxo-2-furanacetic acid. The preparation method disclosed by the invention does not generate nitric oxide and composite salt, and is low in treatment difficulty, low in environmental harm, low in temperature required by the whole reaction, low in energy consumption, simple in reaction step and short in time consumption.
Aroylation of Electron-Rich Pyrroles under Minisci Reaction Conditions
Laha, Joydev K.,Kaur Hunjan, Mandeep,Hegde, Shalakha,Gupta, Anjali
supporting information, p. 1442 - 1447 (2020/02/22)
The development of Minisci acylation on electron-rich pyrroles under silver-free neutral conditions has been reported featuring the regioselective monoacylation of (NH)-free pyrroles. Unlike conventional Minisci conditions, the avoidance of any acid that could result in the polymerization of pyrroles was the key to success. The umpolung reactivity of the nucleophilic acyl radical, generated in situ from arylglyoxylic acid, could help explain the mechanism of product formation with electron-rich pyrroles. Alternatively, the nucleophilic substitution of the acyl radical on the electron-deficient pyrrole radical cation is proposed.
