542-05-2Relevant articles and documents
Unusual tandem sequence of oxa Diels-Alder reaction, retro Diels-Alder reaction, and oxa 6π-electrocyclic ring opening in the reaction of 6-amino-4-(4-methoxyphenyl)-2H-pyran-2-ones with benzaldehydes
Khatri, Adil I.,Samant, Shriniwas D.
, p. 2009 - 2012 (2015)
The oxa Diels-Alder reaction of 6-amino-4-(4-methoxyphenyl)-2H-pyran-2-ones with benzaldehydes took an unusual path whereby a tandem sequence of the oxa Diels-Alder reaction, retro Diels-Alder reaction, and 6π-electrocyclic ring opening of the pyran yielded 3-(4-methoxyphenyl)-5-phenyl-1-(piperidin-1-yl/pyrrolidin-1-yl)penta-2,4-dien-1-ones. The reaction took place in boiling toluene with a series of substituted benzaldehydes. An electron-donating group on benzaldehyde retarded the reaction, while an electron-withdrawing group favoured it, thus indicating the normal electron demand pathway. This journal is
Biocompatible natural sugar-based surfactant assisted oxidation of citric acid by MnO4- in absence and presence of SDS
Khan, Zaheer,Al-Thabaiti, Shaeel Ahmad,Malik, Maqsood Ahmad
, p. 45993 - 46001 (2016)
Crocin, a natural carotenoid with antioxidant properties, was used in the present investigation as a surfactant in the citric acid-MnO4- redox system for the first time. A conventional UV-Visible spectroscopic technique was used to determine the reaction rate with and without crocin. The reaction follows first-order kinetics with respect to [citric acid] under pseudo-first conditions. Crocin was found to catalyze the redox reaction, which was rationalized in terms of the solubilization and/or incorporation of reactants into the crocin aggregates. The micellar catalysis was explained using Menger-Portony pseudo-phase model modified by Bunton et al. The various parameters associated with the micellar catalysis and activation parameters were determined and discussed. Sodium dodecyl sulphate (SDS) inhibits citric acid oxidation. A mixture of non-ionic and anionic surfactant (crocin + SDS) also shows the inhibitory effect rather than catalytic effect. In the mix micellization, the SDS characters and electrostatic repulsion, dominate over the solubilization of reactants in to the Stern layer. On the basis of the observed results, probable mechanisms and reaction sites were proposed.
Effect of metal ions on acetone dicarboxylic acid catalyzed peroxomonosulphate reactions
Ragukumar,Andal,Murugavelu,Lavanya,Ramachandran
, p. 22 - 28 (2014)
The oxidation of Fe(III), Ni(II) and Co(II) citrates by peroxomonosulphate (PMS) in the pH range 3.0-6.0 follows autocatalysis mechanism. The acetone dicarboxylic acid (ADC), the oxidative decarboxylation product from citrate, is found to catalyze the reaction. The added metal ions switch the reaction from the ADC catalyzed decomposition of PMS to the oxidation of citrates. Based on the results from alcohol quenching, a mechanism involving oxygen atom transfer is proposed.
Organic Substrates Producing a Dual-Frequency Belousov-Zhabotinskii Oscillating Reaction
Tsukada, Masao
, p. 1537 - 1540 (1987)
Four organic substrates, acetoacetic acid methyl ester, 4-chloroacetoacetic acid ethyl ester, acetonedicarboxylic acid diethyl ester, and N-methylacetoacetamide, have been found to generate dual-frequency oscillations in the Belousov-Zhabotinskii type reaction system.
Synthetic method of non-steroidal antiinflammatory drug pain killing
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Paragraph 0041-0043; 0055-0057; 0068-0070; 0081-0083; 0094--, (2021/04/17)
The invention discloses a synthesis method of non-steroidal anti-inflammatory drug tolmetin. The methodcomprises the following steps: sequentially preparing a sulfuric acid-containing acetonedicarboxylic acid crude product, 2-(2-acetoxy)-1-methyl-1H-pyrrole-3-formic acid and 2-(2-alkyl acetate)-1-methyl-1H-pyrrole-3-formic acid by taking citric acid or citric acid monohydrate as a raw material; and carrying out decarboxylation, acylation, hydrolysis and acidification to obtain tolmetin. The synthetic method provided by the invention overcomes the defect that the existing tolmetin preparation process depends on N-methylpyrrole, and is a low-cost, low-pollution and high-yield synthetic method of non-steroidal anti-inflammatory drug tolmetin.
Synthesis and antitumor potential of new 7-halocoumarin-4-acetic acid derivatives
Mustafa, Yasser Fakri,Khalil, Raghad Riyadh,Mohammed, Eman Tareq
, p. 3711 - 3716 (2021/07/10)
Compounds having their chemical structure based on coumarin framework have enticed much research concern not only because of the variance structural characteristic but also the pluralism of the bioactivities. In this report, four derivatives of 7-halo-4-coumarinylacetic acid referred to as RY1-RY4 were synthesized, and their chemical backbones were confirmed via the employed spectrophotometers. The pharmacokinetic profiles of the synthesized halocoumarins were inspected in silico using a free online software named the pre-ADMET program. The potential of the synthesized halocoumarins as antitumor applicants was evaluated utilizing 5-fluorouracil as a reference drug and the well-authenticated protocol based on the MTT as a visible indicator against eight standard tumor-cell lines. The outcomes acquired from this assessment indicated that the synthesized halocoumarins, except RY1, have less impact as antitumor agents comparing with the standard drug. Also, the halocoumarins revealed roughly the same fashion of activity versus the test cell lines with the greatest inhibitory influence reported against MCF-7 and HeLa. From the calculated pharmacokinetic data and outcomes exhibited from antitumor assessment, the authors concluded that the synthesized halocoumarins, particularly RY1, offered potential applicants as antitumor agents with broad-ranged activity. Besides, the compounds RY1 and RY2 may provide highly valuable scaffolds for synthesizing agents with a powerful antitumor activity versus the breast and cervical cancer phenotypes.
Deciphering the Biosynthetic Mechanism of Pelletierine in Lycopodium Alkaloid Biosynthesis
Abe, Ikuro,Ding, Ning,Hnin, Saw Yu Yu,Jiang, Fang-Fang,Li, Jun,Liu, Xiao,Morita, Hiroyuki,Qi, Bo-Wen,Shi, She-Po,Tu, Peng-Fei,Wang, Juan,Wang, Xiao-Hui,Zhang, Ze-Kun
, (2020/11/13)
Pelletierine, a proposed building block of Lycopodium alkaloids (LAs), was demonstrated to be synthesized via the non-enzymatic Mannich-like condensation of Δ1-piperideine and 3-oxoglutaric acid produced by two new type III PKSs (HsPKS4 and PcPKS1) characterized from Huperzia serrata and Phlegmariurus cryptomerianus, respectively. The findings provide new insights for further understanding the biosynthesis of LAs such as huperzine A.
Method for preparing silicon compounds
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Paragraph 0079; 0081; 0082; 0083; 0084; 0085, (2019/11/14)
The invention provides a method for preparing silicon compounds, and belongs to the field of chemical synthesis. The method for preparing the silicon compounds comprises the following processes that citric acid is used as a raw material for performing oxidative decarboxylation to obtain a compound 1,3-acetone dicarboxylic acid; esterification reaction is carried out to obtain a compound 1,3-acetone dicarboxylic acid dimethyl ester; catalytic hydrogenation reduction is carried out to obtain a compound 3-hydroxyglutaric acid dimethyl ester; etherification reaction is carried out to obtain a compound3-tertiary butyl dimethyl siloxy dimethyl glutarate; saponification, dehydration and purification are carried out to obtain 3-tert-butyl-dimethylsiloxyglutaric anhydride; and a catalyst for catalytic hydrogenation is Cu/ZnO/Al2O3 prepared by a precipitation reduction method. According to the method for preparing the silicon compounds, the catalyst for catalytic hydrogenation is optimized, so that in the hydrogenation reduction reaction, the hydrogenation activity of a Cu catalyst is significantly improved, the selectivity is increased, and the generation of by-products is reduced; and theproduct yield and purity are significantly improved by recrystallization with a mixed solvent.
Preparation method for anticholinergic drug intermediate
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Paragraph 0016; 0017; 0018; 0019; 0020; 0021; 0022; 0023, (2019/01/08)
The invention discloses a preparation method for an anticholinergic drug intermediate. Acetone-dicarboxylic acid is a common intermediate for synthesizing medicines, and has a very high application value in organic synthesis. The preparation method comprises the following steps: using citric acid monohydrate as a starting raw material, using concentrated sulfuric acid as a dehydrating agent, and adding a suitable amount of a water absorbent. The method is capable of saving resources, and saving cost, stable in product quality and high in yield, and suitable for large-scale stable industrial production.
Synthetic method for drug intermediate acetonedicarboxylic acid
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Paragraph 0011; 0014-0017; 0018-0021; 0022-0025, (2018/07/30)
The invention discloses a synthetic method for the drug intermediate acetonedicarboxylic acid. The synthetic method comprises the following steps: adding 2-methoxypropane-1,3-dicarboxylic acid and a sodium nitrate solution into a reaction vessel, increasing the temperature of the obtainded solution, adding lead tetraacetate in batches, controlling a stirring speed and continuing a reaction; and then adding zinc oxalate powder, continuing the reaction, carrying out cooling, carrying out washing with a potassium chloride solution, carrying out washing with a diphenyl ether solution, then carrying out recrystallization in a diethylene glycol solution, and carrying out dehydration with a dehydrating agent so as to obtain the finished acetonedicarboxylic acid.
