- Convergent Synthesis of Dihydropyrans from Catalytic Three-Component Reactions of Vinylcyclopropanes, Diazoesters, and Diphenyl Sulfoxide
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A novel Rh(I)/La(III) cocatalytic three-component reaction of vinylcyclopropanes, diazoesters, and diphenyl sulfoxide has been developed. The reaction gives polysubstituted dihydropyrans as the reaction products. Mechanistic studies indicate that isomerization of vinylcyclopropanes gives conjugated dienes, which then undergo [4 + 2]-cycloaddition with vicinal tricarbonyl compounds generated by oxygen atom transfer from diphenyl sulfoxide to diazoesters.
- Zhang, Ya-Lin,Guo, Rui-Ting,Luo, Heng,Liang, Xin-Shen,Wang, Xiao-Chen
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supporting information
p. 5627 - 5632
(2020/07/14)
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- Synthetic method of diacetate mono-hydrate of ketomalonic acid (by machine translation)
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The reaction solution is slowly cooled to room temperature and stirred overnight under a weak acid and water environment, and the obtained reaction solution B is stirred at room temperature and stirred overnight, and after the A reaction is finished, the required compound of diethyl malonate monohydrate is obtained through extraction, 50 - 80 °C washing, drying, filtration and concentration 3 - 5 B. The synthesis method of the diacetate mono-hydrate of the ketomalonic acid has the advantages of simple reaction, easily available A raw materials, simple post-treatment, low cost, strong B operability and high industrial value. (by machine translation)
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Paragraph 0016-0017
(2019/11/28)
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- PRODUCTION METHOD OF KETOMALONIC ACID COMPOUND
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Provided is a method for producing an industrially useful ketomalonic acid compound such as ketomalinic acid diesters, or a hydrate thereof, by a method more favorable from an economic and environmental standpoint and from a safety standpoint. The present invention relates to a method involving reacting a malonic acid compound represented by general formula (1) (in the formula, The each Rs indicate an alkyl group, a cycloalkyl group, etc.) with chlorine dioxide to produce a ketomalonic acid compound represented by the general formula (2) (in the formula, R has the same meaning as above), or a hydrate thereof.
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Paragraph 0212; 0213; 0214; 0215; 0216; 0217; 0218-0220
(2016/08/10)
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- Production method of ketomalonic acid compound
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Provided is a method for producing an industrially useful ketomalonic acid diesters or other ketomalonic acid compound, or a hydrate thereof, by a method more favorable from an economic and environmental standpoint and from a safety standpoint. The present invention relates to a method involving reacting a malonic acid compound represented by general formula (1) (in the formula, the Rs indicate an alkyl group, a cycloalkyl group, etc.) with chlorine dioxide to produce a ketomalonic acid compound represented by the general expression (2) (in the formula, R has the same meaning as above), or a hydrate thereof.
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Paragraph 0232; 0233; 0237; 0238; 0239; 0240; 0241-0245
(2016/12/07)
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- Facile synthesis of 1,2,3-tricarbonyls from 1,3-dicarbonyls mediated by cerium(IV) ammonium nitrate
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A mild and efficient protocol for the synthesis of vicinal tricarbonyl compounds from β-dicarbonyls in a single step using cerium(IV) ammonium nitrate as a catalytic oxidant is described. Ease of execution, wide substrate scope and the suitability for the synthesis of commercially important compounds like ninhydrin, alloxan and oxoline make this reaction particularly noteworthy.
- Sivan, Akhil,Deepthi, Ani
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supporting information
p. 1890 - 1893
(2014/03/21)
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- PROCESS FOR PRODUCTION OF KETOMALONIC ACID COMPOUNDS OR HYDRATES THEREOF
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Disclosed is a process for the production of ketomalonic acid compounds or hydrates thereof by reacting a malonic acid compound with one or more chlorous acid compounds selected from among chlorous acid and chlorites and thus oxidizing the methylene group of the malonic acid compound. The process does not necessitate highly toxic reagents, lowly safe reagents, special reactants, special reaction equipment, expensive reagents, expensive catalysts, or transition metals such as noble metals, and permits the selection of mild reaction conditions and simple operation, thus enabling efficient and easy production of ketomalonic acid compounds such as ketomalonic diesters under simple and easy conditions suitable for industrialization.
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Page/Page column 8
(2012/01/14)
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- Preparation process for alpha , beta -dicarbonylated compounds
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Preparation process for alpha , beta -dicarbonylated compounds of formula (I) in which R2=alkyl, phenyl or benzyl being able to be substituted in various ways on the cycle, or carboxylic ester, and R3=alkyl or alkoxy or carboxylic ester in which a compound of formula (II) in which R1=alkyl, or alkyl alpha -ketocarboxylate or carboxylic ester, and R2 and R3 have the same meanings as previously is reacted in a nitrile type solvent, with molecular oxygen in the presence of copperII nitrate or ferric chloride as catalyst, and use for obtaining ethyl alpha -ketobutyrate, ethyl phenyl pyruvate, ethyl pyruvate, ethyl phenylglyoxylate, butane-2,3-dione or diethyl mesoxalate.
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- CHEMISTRY OF NITRO ESTERS XVII. METHOD FOR THE PRODUCTION OF MESOXALIC ESTERS
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A new preparative method was developed for the production of mesoxalic esters from bromomalonic esters and silver nitrate
- Kochergin, P. M.,Titkova, R. M.
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p. 1042 - 1044
(2007/10/02)
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- Process for the preparation of monocarbonyl or biscarbonyl compounds
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The invention relates to a process for the preparation of monocarbonyl or biscarbonyl compounds by reacting organic carbon compounds having one or more olefinic or aromatic double bonds in the molecule with the equivalent amount of ozone and by subsequently catalytically hydrogenating the ozonization products, wherein the peroxide-containing ozonization solution is fed continuously into a suspension of the hydrogenation catalyst in a lower aliphatic alcohol, while a peroxide content of not more than 0.1 mole/l is maintained, and the ozonization products are continuously cleaved reductively to give the corresponding carbonyl compounds.
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- Synthesis and Biological Activity of Heterocyclic Derivatives derived from Ethyl-2-hydroxyquinoxaline-3-carboxylate
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Ethyl-2-chloroquinoxaline-3-carboxylate obtained from ethyl-2-hydroxyquinoxaline-3-carboxylate upon treatment with morpholine gave ethyl-2-morpholinoquinoxaline-3-carboxylate (1).This ester upon reaction with hydrazine hydrate (99percent) gave respective carboxy hydrazide (2).This hydrazide on reaction with phenyl isothiocyanates gave thiosemicarbazides (3a-c).The thiosemicarbazides on reaction with concentrated sulphuric acid or anhydrous phosphoric acid gave 2-(4-substituted)-anilino-5-((2'-morpholino)quinoxalino)-1,3,4-thiadiazoles (4a-c).The thiosemicarbazides on reaction with 4percent sodium hydroxide formed 4-(para-substituted-phenyl)-3-mercapto-5-((2'-morpholino)quinoxalino)-1,2,4-triazoles (5a-c), and on reaction with I2 in KI gave 2-(4-substituted)anilino-5-((2'-morpholino)quinoxalino)-1,3,4-oxadiazoles (6a-c) respectively.
- Fernandes, P. S.,Sonar, T. M.
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p. 427 - 429
(2007/10/02)
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- Process for preparing carbonyl compounds
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There is described a process for preparing carbonyl compounds of formula: STR1 by oxidation of compounds of formula: STR2 wherein X=--CN, --COOR, Y=--COOR1, --CN, and R, R1, like or unlike each other, are inert radicals, by employing oxygen or air as oxidants, at least a catalyst selected from the salts of organic or inorganic acids of Mn, Co, Cu and Fe, from 0 to 60 moles of an alkaline salt of an aliphatic carboxylic acid per gram-atom of catalyst metal, in a polar solvent, at temperatures ranging from 30° C. to 200° C. and maintaining the reaction medium anhydrous. The present invention relates to a process for preparing carbonyl compounds by catalytic oxidation of compounds containing an activated methylene group.
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- THE USE OF NITRATE ESTERS IN THE SYNTHESIS OF DI- AND TRI-CARBONYL COMPOUNDS
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Vicinal di- and tri-carbonyl compounds are prepared by reacting some electrophiles, bearing a C=O vicinal to the leaving group, with an anion exchanger, in the nitrate form, or with the ammonium salt n-Bu4N(+)NO3(-).
- Cainelli, Gianfranco,Manescalchi, Francesco,Plessi, Laura
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p. 163 - 164
(2007/10/02)
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- Heterocycles from α-Nitroolefins, VIII. - 2-Methyl-3-pyrrolecarboxylates from α-Nitroolefins and Acetoacetates
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3-Pyrrolecarboxylates 4 can be prepared from α-nitroolefins 1 and acetoacetates 2 by two methods: (a) 1 and 2 react to give 4,5-dihydro-5-methyleneamino-3-furancarboxylates 3 which are hydrolyzed, (b) the nitronic acids 8, adducts of 1 and 2, yield with different reduction agents the heterocycles 4.
- Boberg, Friedrich,Garburg, Karl-Heinz,Goerlich, Karl-Joachim,Pipereit, Eberhard,Ruhr, Maria
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p. 239 - 250
(2007/10/02)
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- VICINAL TRICARBONYL PRODUCTS FROM SINGLET OXYGEN REACTIONS. APPLICATION TO THE SYNTHESIS OF CARBACEPHAMS.
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Vicinal tricarbonyl systems are readily formed by reacting β-dicarbonyl precursors with DMF acetal to form enamines which are then cleaved by photooxidation.This procedure may be applied to the formation of carbacephams.
- Wasserman, Harry H.,Han, William T.
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p. 3743 - 3746
(2007/10/02)
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- ELECTROGENERATED BASES VII. NOVEL SYNTHESES OF ETHYL GLYOXALATE AND DIETHYL KETOMALONATE VIA ELECTROGENERATED SUPEROXIDE
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Using electrogenerated tetraalkylammonium superoxide plus oxygen ethyl cyanoacetate has been converted (a) directly to ethyl glyoxylate and (b) in a "one-pot" two-step synthesis to the oxomalonate.
- Sugawara, M.,Baizer, M. M.
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p. 2223 - 2226
(2007/10/02)
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- Introduction of Oxygen Functions into the α-Position of β-Diketons. 7.Oxo-Meldrum's Acids by Ozonolytic Cleavage of (Methoxymethylene)-Meldrum's Acids
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(Methoxymethylene)-Meldrum's acids 1 react with ozone in aprotic medium to form the corresponding sec. ozonides 2 ("peroxyorthoformates").Deoxygenation of 2 with PCl3 yields Oxo-Meldrum's acids 3.
- Schank, Kurt,Schuhknecht, Christoph
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p. 2000 - 2002
(2007/10/02)
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- PREPARATION OF DI- AND TRIACYLIMINES AND THEIR USE IN THE SYNTHESIS OF NITROGEN HETEROCYCLES
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Reaction of aza-Wittig reagents with glyoxylates and keto malonates produces di- and triacylimines which are moderately reactive dienophiles for Diels-Alder cycloaddition.
- Jung, Michael E.,Shishido, Kozo,Light, Lynn,Davis, Leonard
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p. 4607 - 4610
(2007/10/02)
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