cas 6148-64-7, Ethyl potassium malonate | Articles data

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Kinetic study of the Ce(III)-, Mn(II)- or Fe(phen)32+-catalyzed Belousov-Zhabotinsky reaction with ethyl hydrogen malonate
In a stirred batch reaction, Fe(phen)32+ ion behaves differently from Ce(III) or Mn(II) ion in catalyzing the bromate-driven oscillating reaction with ethyl hydrogen malonate [CH2COOHCOOEt, ethyl hydrogen malonate (EHM)]. The effects of N2 atmosphere, concentrations of bromate ion, EHM, metal ion catalyst, sulfuric acid, and additive (bromide ion or bromomalonic acid) on the pattern of oscillations were investigated. The kinetic study of the reaction of EHM with Ce(IV), Mn(III), or Fe(phen)33+ ion indicates that under aerobic or anaerobic conditions the order of reactivity toward reacting with EHM is Mn(III)>Ce(IV)?Fe(phen)33+, which follows the same trend as that of the malonic acid system. The presence of the ester group in EHM lowers the reactivity of the two methylene hydrogen atoms toward bromination or oxidation by Ce(IV), Mn(III), or Fe(phen)33+ ion. No good oscillations were observed for the BrO3-CH2(COOEt)2 reaction catalyzed by Ce(III), Mn(II), or Fe(phen)32+ ion. A discussion of the effects of oxygen on the reactions of malonic acid and its derivatives (RCHCOOHCOOR′) with Mn(III), Fe(phen)33+ ion is also presented.
Hsu,Jwo,Jwo
p. 52 - 61
(2000)
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Continuous Flow Electrochemical Oxidative Cyclization and Successive Functionalization of 2-Pyrrolidinones
2-Pyrrolidinones are important scaffolds found in numerous pharmacologically active compounds, such as brivaracetam and levetiracetam (antiepileptic drugs) or piracetam and pramiracetam (age-related memory impairment drugs). Among the numerous targets, nootropic agents represent an attractive class of compounds since they selectively improve cognitive functions. In this study, we report the successful translation of an electrochemical batch oxidative cyclization/functionalization of 2-pyrrolidinones, using the Kolbe reaction, from a batch type cell to a continuous flow electrochemical reactor. Combining organic electrosynthesis with continuous flow chemistry offers numerous advantages over batch electrolysis such as a faster reaction time and better mixing of the heterogeneous reaction. Moreover, due to the use of continuous flow electrochemical cells, which have a precise geometry, a small interelectrode gap, and large electrode surface area to reactor volume ratio, the productivity of organic electrosynthesis can be easily improved. Additionally, the translation of a batch electrochemical transformation to a continuous flow reactor is a critical step in the development of an electrochemical process given that flow chemistry is the most straightforward approach for the scale-up of this type of reactions. In this study, the application of continuous flow electrochemistry in our process allowed for an excellent productivity of 0.40 g/(h·mL) and an up to 81% yield of 2-pyrrolidinone within a loop-reactor setup (equipped with a 5 mL container).
Quertenmont, Mathilde,Toussaint, Frédéric C.,Defrance, Thierry,Lam, Kevin,Markó, István E.,Riant, Olivier
supporting information
p. 2631 - 2638
(2021/11/24)

Structure-based linker optimization of 6-(2-cyclohexyl-1-alkyl)-2-(2-oxo-2-phenylethylsulfanyl)pyrimidin-4(3H)-ones as potent non-nucleoside HIV-1 reverse transcriptase inhibitors
In continuation of our efforts toward the discovery of potent HIV-1 NNRTIs with diverse structures, a series of novel S-DACO analogues of 6-(2-cyclohexyl-1-alkyl)-2-(2-oxo-2-phenyl-ethylsulfanyl)pyrimidin-4(3H)-ones were designed, synthesized and evaluated for their antiviral activities in MT-4 cells. Most of these new compounds showed moderate to good activities against wild type HIV-1 with IC50 values ranging from 7.55 μmol/L to 0.018 μmol/L. Among them, compound 5c was identified as the most promising inhibitor against HIV-1 replication with an IC50 = 0.018 μmol/L, CC50 = 194 μmol/L, and SI = 12791, which was much more potent than the reference drugs NVP and DLV and comparable to AZT and EFV. In addition, 5c also exhibited improved activity against double mutant HIV-1 strain RES056 compared to that of the reference drugs NVP/DLV and DB02. The preliminary structure-activity relationship (SAR) and molecular modeling studies were also discussed, which provides some useful indications for guiding the further rational design of new S-DACO analogues.
Li, Daxiong,Zhang, Chunsheng,Ding, Wei,Huang, Siming,Yu, Le,Lu, Nan,Pan, Wenkai,Li, Yiming,De Clercq, Erik,Pannecouque, Christophe,Zhang, Hongbing,Wang, Yueping,He, Yanping,Chen, Fener
supporting information
p. 1020 - 1024
(2020/10/12)

Kolbe Anodic Decarboxylation as a Green Way to Access 2-Pyrrolidinones
Nootropic compounds are a group of pharmacologically active pyrrolidones. These molecules, which enhance cognition properties and possess a large prescription field, are particularly interesting synthetic targets for the pharmaceutical industry. In this Article, we disclose an effective and environmentally friendly pyrrolidinone synthesis using electrosynthesis. The newly developed methodology includes a Kolbe decarboxylation, followed by an intramolecular radical cyclization and a radical-radical cross-coupling.
Goodall, Iain,Lam, Kevin,Markó, István,Quertenmont, Mathilde,Riant, Olivier
supporting information

(2020/03/04)

Method for preparing urea-based pyrimidone precursor
The invention discloses a urea-based pyrimidone precursor compound and a synthetic method thereof. The urea-based pyrimidone precursor is an isoheptyl substituted isocytosine compound. The specific synthetic method comprises the following steps: synthesizing diethyl potassium malonate, synthesizing 2-ethylhexanoyl chloride, synthesizing beta-keto ester from the diethyl potassium malonate and 2-ethylhexanoyl chloride, and synthesizing the urea-based pyrimidone precursor from the beta-keto ester and guanidine carbonate. The urea-based pyrimidone precursor compound and the synthetic method thereof disclosed by the invention have the beneficial effects that the urea-based pyrimidone precursor provides a basic raw material for preparation of a multiple hydrogen bonding supra-molecular material,and the method is controllable in synthetic process and capable of saving resources and improving the yield, and has excellent application prospects.
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Paragraph 0017

(2019/04/06)

Derivatisation of parthenolide to address chemoresistant chronic lymphocytic leukaemia
Parthenolide is a natural product that exhibits anti-leukaemic activity, however, its clinical use is limited by its poor bioavailability. It may be extracted from feverfew and protocols for growing, extracting and derivatising it are reported. A novel parthenolide derivative with good bioavailability and pharmacological properties was identified through a screening cascade based on in vitro anti-leukaemic activity and calculated "drug-likeness" properties, in vitro and in vivo pharmacokinetics studies and hERG liability testing. In vitro studies showed the most promising derivative to have comparable anti-leukaemic activity to DMAPT, a previously described parthenolide derivative. The newly identified compound was shown to have pro-oxidant activity and in silico molecular docking studies indicate a prodrug mode of action. A synthesis scheme is presented for the production of amine 7 used in the generation of 5f.
Li, Xingjian,Payne, Daniel T.,Ampolu, Badarinath,Bland, Nicholas,Brown, Jane T.,Dutton, Mark J.,Fitton, Catherine A.,Gulliver, Abigail,Hale, Lee,Hamza, Daniel,Jones, Geraint,Lane, Rebecca,Leach, Andrew G.,Male, Louise,Merisor, Elena G.,Morton, Michael J.,Quy, Alex S.,Roberts, Ruth,Scarll, Rosanna,Schulz-Utermoehl, Timothy,Stankovic, Tatjana,Stevenson, Brett,Fossey, John S.,Agathanggelou, Angelo
supporting information
p. 1379 - 1390
(2019/08/20)

Method for preparing potassium monoethyl malonate
The invention provides a method for preparing potassium monoethyl malonate. According to the method, a compound in a malonate monoester series is used as a raw material to react with potassium bicarbonate to obtain the potassium monoethyl malonate. The invention opens up a new way to prepare potassium monoethyl malonate series under a very mild condition in a safe and environment-friendly mode, and the method is suitable for industrial production and meets the market demands of the compound.
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Paragraph 0025

(2019/02/27)

Pyrazole alcohol compound, pharmaceutical composition thereof and application thereof to drugs
The invention discloses a 1-(3,5,6-trimethyl pyrazine-2-yl)-5-pyrazole alcohol compound, a tautomer thereof, a pharmaceutical composition thereof and application thereof to drugs. The 1-(3,5,6-trimethyl pyrazine-2-yl)-5-pyrazole alcohol compound has double effects of resisting platelet aggregation and protecting nerve cells, and comprises a compound as shown in the formula (I), a tautomer (Ia) thereof, or a stereoisomer, a geometrical isomer, a hydrate or a solvate thereof, or a pharmaceutically acceptable salt or prodrug as shown in the description. The 1-(3,5,6-trimethyl pyrazine-2-yl)-5-pyrazole alcohol compound and the pharmaceutical composition thereof provided by the invention can be used for preparing drugs for prevention and/or treatment and/or auxiliary treatment of cerebral apoplexy, cardiovascular and cerebrovascular diseases, senile dementia and complications thereof caused by thrombosis and excessive free radicals.
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Paragraph 0119; 0127

(2018/10/19)

Preparation method for polyfluoromethylpyrazole compound, and intermediate of compound and preparation method thereof
The invention discloses a preparation method for a polyfluoromethylpyrazole compound, and an intermediate of the compound and a preparation method thereof. The invention provides a preparation method for a compound 1 as defined in the specification. The preparation method comprises a step of subjecting a compound 2 as defined in the specification and methylhydrazine to a ring-closure reaction in an organic solvent so as to obtain the compound 1, wherein R is a C1-4 alkyl group, R is a methyl or ethyl group and x is 2 or 3. The preparation method provided by the invention uses cheap and easily available raw materials and is mild in reaction conditions, safe to operate, environment friendly, low in production cost, high in reaction conversion rate, low in the content of isomer in by-products, high in reaction yield and product purity and suitable for industrial production.
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Paragraph 0126; 0127; 0128

(2017/06/30)

Silver-Catalyzed Cyclization of Propargylic Amides to Oxazolines
A ligand-accelerated effect is observed in the cyclization of propargylic amides catalyzed by bis(pyridyl)silver(I) complexes, with an unexpected reversal of electronic demand to the analogous NH addition reaction. The catalyst was found to be effective for internal alkyne substrates, offering exclusive selectivity for the 5-exo-dig product. Differences in selectivity profile between gold- and silver-catalyzed processes are highlighted and discussed.
Wong, Valerie H. L.,White, Andrew J. P.,Hor,Hii
supporting information
p. 3943 - 3948
(2016/01/25)

SUBSTITUTED TRICYCLIC COMPOUNDS AS FGFR INHIBITORS
The present invention relates to tricyclic compounds, and pharmaceutical compositions of the same, that are inhibitors of one or more FGFR enzymes and are useful in the treatment of FGFR-associated diseases such as cancer.
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Page/Page column 140

(2014/01/18)

PROCESS FOR PREPARING SODIUM SALTS OR POTASSIUM SALTS OF 4-HYDROXY-2-OXO-2,5-DIHYDROFURAN-3-CARBOXYLATE
Process for preparing sodium or potassium salts of 4-hydroxy-2-oxo-2,5-dihydrofuran-3-carboxylic esters, comprising the reaction of a malonic ester with potassium hydroxide to give the corresponding malonic ester potassium salt of the formula (III) which is then reacted further with a chloroacetic ester to give a compound of the formula (V) followed by a ring closure reaction in which the compound of the formula (V) is reacted with a sodium or potassium alkoxide of the formula ZOR1 where R1, R2, R3 and K are each as defined in the description.
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Paragraph 0037

(2014/06/11)

PROCESS FOR THE PREPARATION OF ( S ) - 3 - CYANO - 5 - METHYLHEXANOIC ACID DERIVATIVES ADN OF PREGABALIN
The invention provides a process for the manufacture of a compound of formula (I) using an enzyme catalysed reduction of a compound of formula (lla) or llb). Compounds of formula (I) are useful for preparing pregabalin.
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Page/Page column 20

(2012/03/26)

Pd-catalyzed decarboxylative cross-couplings of potassium malonate monoesters with aryl halides
An efficient catalytic protocol for Pd-catalyzed decarboxylative cross-coupling of potassium malonate monoesters and derivatives with aryl bromides and chlorides are described. Because of its broad applicability, this new catalytic system provides an alternative method for the preparation of diverse aryl acetic acids and derivatives.
Feng, Yi-Si,Wu, Wei,Xu, Zhong-Qiu,Li, Yan,Li, Ming,Xu, Hua-Jian
supporting information; experimental part
p. 2113 - 2120
(2012/03/26)

Synthesis of α-Aryl nitriles through palladium-catalyzed decarboxylative coupling of cyanoacetate salts with aryl halides and triflates
Worth its salt: The palladium-catalyzed decarboxylative coupling of the cyanoacetate salt as well as its mono- and disubstituted derivatives with aryl chlorides, bromides, and triflates is described (see scheme). This reaction is potentially useful for the preparation of a diverse array of α-aryl nitriles and has good functional group tolerance. S-Phos=2-(2,6- dimethoxybiphenyl)dicyclohexylphosphine), Xant-Phos=4,5-bis(diphenylphosphino)- 9,9-dimethylxanthene. Copyright
Shang, Rui,Ji, Dong-Sheng,Chu, Ling,Fu, Yao,Liu, Lei
supporting information; experimental part
p. 4470 - 4474
(2011/06/24)

Stereoselective control in the Staudinger reactions involving monosubstituted ketenes with electron acceptor substituents: Experimental investigation and theoretical rationalization
The stereoselectivity of the Staudinger reactions involving monosubstituted ketenes with electron acceptor substituents was investigated experimentally by determination of the product stereochemistry and theoretically via DFT calculations. The results indicate that imines preferentially attack the less sterically hindered exo-side of the ketenes to generate zwitterionic intermediates. Subsequently, for cyclic imines, the intermediates undergo a conrotatory ring closure directly to produce β-lactams, while for linear imines, the imine moiety of the intermediates isomerizes to more stable intermediates, which further undergo a conrotatory ring closure to afford trans-β-lactams. The steric hindrance and the isomerization, rather than the torquoelectronic effect, play crucial roles in controlling the stereoselectivity in the practical Staudinger reactions involving monosubstituted ketenes with electron acceptor substituents, although the unaccessible borylketene with a powerful electron acceptor group controls the stereoselectivity torquoelectronically, in theory.
Qi, Hengzhen,Li, Xinyao,Xu, Jiaxi
supporting information; experimental part
p. 2702 - 2714
(2011/05/19)

Design, synthesis, and evaluation of aza inhibitors of chorismate mutase
The detailed information pertaining to this panel of aza inhibitors is presented. A series of aza inhibitors (4-9) of chorismate mutase (E.C. 5.4.99.5) was designed, prepared, and evaluated against the enzyme by monitoring the direct inhibition of the chorismate, 1, to prephenate, 2, conversion. None of these aza inhibitors displayed tighter binding to the enzyme than the native substrate chorismate or greater inhibitory action than the previously reported ether analogue, 3. Furthermore, no time-dependent loss of enzyme activity was observed in the presence of the two potentially reactive aza inhibitors (7 and 9). These results in conjunction with inhibition data from a broader series of chorismate mutase inhibitors allowed a novel proposal for the mechanistic role of chorismate mutase to be developed. This proposed mechanism was computationally verified and correlated with crystallographic studies of various chorismate mutases.
Hediger, Mark E.
p. 4995 - 5010
(2007/10/03)

Helical supramolecular aggregates based on ureidopyrimidinone quadruple hydrogen bonding
A series of mono- and bi-functional compounds 2-7, based on the ureido pyrimidinone quadruple hydrogen bonding unit, was prepared to study the mode of aggregation of these compounds in the bulk and in solution. Compounds 2-7 exhibit thermotropic liquid crystalline properties, as evidenced by differential scanning calorimetry and optical polarization microscopy. The presence of an ordered hexagonal discotic (Dho) phase of 2a was confirmed by X-ray diffraction on an aligned sample. In chloroform, the bi-functional compounds form cyclic dimers at millimolar concentrations, and these dimers exist in equilibrium with linear species above a critical concentration, which may be from 6 mM to greater than 260 mM, depending on the structure of the spacer. Circular dichroism measurements in chloroform did not show a Cotton effect. Dodecane solutions of compounds 3, 4b, and 7b display a Cotton effect at the absorption band of the phenyl-pyrimidinone unit. Amplification of chirality was observed in mixtures of 7a and 7b, but not in mixtures of 4a and 4b, indicating that 7a and 7b form mixed polymeric aggregates with a helical architecture in dodecane solution, whereas 4a and 4b do not. The Cotton effect is lost upon increasing the temperature. Half of the helicity is lost at 25°C for 3 and at 60°C for 4b, suggesting that 3, bearing the shorter spacer, forms less stable columns than 4b. Compound 7b loses half of its helicity at 45°C. Compounds 2b, 5, and 6 do not exhibit helical organization, as evidenced by the absence of Cotton effects.
Hirschberg, J. H. K. Ky,Koevoets, Rolf A.,Sijbesma, Rint P.,Meijer
p. 4222 - 4231
(2007/10/03)

Src kinase inhibitor compounds
Pyrimidine compounds (Formula I), or their pharmaceutically acceptable salts, hydrates, solvates, crystal forms and individual diastereomers, and pharmaceutical compositions including the same, which are inhibitors of tyrosine kinase enzymes, and as such are useful in the prophylaxis and treatment of protein tyrosine kinase-associated disorders, such as immune diseases, hyperproliferative disorders and other diseases in which inappropriate protein kinase action is believed to play a role, such as cancer, angiogensis, atheroscelerosis, graft rejection, rheumatoid arthritis and psoriasis.
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(2008/06/13)

Process for preparation of dicarboxylic acid monoesters
A process for producing a dicarboxylic acid monoester which comprises subjecting a dicarboxylic acid monoester or an alkali metal salt of a dicarboxylic acid monoester and a metal alkoxide to transesterification in the presence of an organic solvent, or a process for producing a dicarboxylic acid monoester which comprises subjecting a dicarboxylic acid monoester or an alkali metal salt of a dicarboxylic acid monoester and an alcohol to transesterification in the presence of a metal alkoxide.
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(2008/06/13)

Synthesis of bone-targeted oestrogenic compounds for the inhibition of bone resorption
Syntheses have been realised for several members of a new class of potential bone resorption inhibitors consisting of steroidal oestrogenic compounds linked at the 17 position to a geminal bis(phosphonic acid) moiety through an ester linkage. The approach used has the potential to allow other biologically active compounds to be coupled to the geminal bisphosphonate unit.
Bulman Page, Philip C,Moore, Jonathan P.G,Mansfield, Ian,McKenzie, Michael J,Bowler, Wayne B,Gallagher, James A
p. 1837 - 1847
(2007/10/03)

2-(pyrazol-5-yl-oxymethyl)-1,2-benzisothiazol-3 (2H)-One 1, 1-dioxides and compositions and method of use thereof
2-(Pyrazol-5-yl-oxymethyl)-1,2-benzisothiazol-3(2H)-one 1,1-dioxides, pharmaceutical compositions containing them and methods for the treatment of degenerative diseases utilizing them.
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(2008/06/13)

Cyclohexyloxycarbonylacetohydrazides and method for producing 1H-1,2,4-triazoles using the hydrazides
There is disclosed cyclohexyloxycarbonylacetohydrazides of formula (I): ???wherein R1represents a hydrogen atom or an alkyl group; R2, R3, R4, R2', R3', and R4', which are the same or different, each represent an alkyl group; R2and R3, and R2' and R3, each may bond together to form a ring; and R5and R6, which are the same or different, each represent a hydrogen atom, a halogen atom, an alkyl group, or an aryl group. The above hydrazides of formula (I) provided are novel compounds useful for producing 1H-1,2,4-triazole derivatives, which latter are synthetic intermediates of physiologically active substances, such as medicines and pesticides, and which latter are also synthetic intermediates of photographic couplers or dyes.
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(2008/06/13)

THE SYNTHESIS OFβ-LACTONES AND β-LACTAMS FROM MALONATES AND MALONAMIDES
The rhodium diacetate induced insertion reactions of some simple esters and amides of diazomalonic acid result in the formation of β-lactones and β-lactams.
Box, Vernon G. S.,Marinovic, Nash,Yiannikouros, George P.
p. 245 - 251
(2007/10/02)