- Rapid assembly of α-ketoamides through a decarboxylative strategy of isocyanates with α-oxocarboxylic acids under mild conditions
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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.
- Huang, Junjie,Liang, Baihui,Chen, Xiuwen,Liu, Yifu,Li, Yawen,Liang, Jingwen,Zhu, Weidong,Tang, Xiaodong,Li, Yibiao,Zhu, Zhongzhi
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supporting information
p. 4783 - 4787
(2021/06/11)
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- Synthesis method of alpha-ketoamide compound
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The invention discloses a synthesis method of an alpha-ketoamide compound. The preparation method comprises the following steps of: taking an isocyanate compound as shown in a formula I and a benzoylformic acid compound as shown in a formula II as raw mat
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Paragraph 0138-0144
(2020/12/09)
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- Synthetic method of alpha-keto amide compound
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The invention discloses a synthesis method of an alpha-keto amide compound, which comprises the following steps: mixing a benzoyl azide compound as shown in a chemical formula I with a benzoyl formicacid compound as shown in a chemical formula II, and reacting to obtain an alpha-keto amide compound as shown in a chemical formula III; in the formula, R1 is a monosubstituted or polysubstituted group on a benzene ring; R2 is a group that is not H; the synthesis method can be used for efficiently synthesizing the functionalized alpha-ketoamide compound, has the advantages of simple synthesis steps, safety in operation, good compatibility of the synthesis method to functional groups and high atom economy, and is easy for industrial synthesis.
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Paragraph 0189-0194
(2020/09/23)
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- Alkyl keto-amide, amidoxime compound thereof, and preparation and application of compound
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The invention relates to alkyl keto-amide, an amidoxime compound thereof, and preparation and application of the compound. The alkyl keto-amide compound and a derivative thereof can be applied to metal palladium catalyzed C-H bond fluoridation, better rea
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Paragraph 0038
(2019/01/23)
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- Catalyst-free three-component synthesis of highly functionalized 2,3-dihydropyrroles
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An efficient synthesis of fully substituted 2,3-dihydropyrroles has been achieved in one step through the three-component reaction of amines, aromatic aldehydes and α-ketoamides. This atom-economical and catalyst-free reaction is highly stereoselective and generates underexplored heterocycles in a single step. These compounds were examined in an enzymatic assay that led to the identification of potent α-glucosidase inhibitors, thereby demonstrating the utility of this novel methodology in medicinal chemistry.
- Wang, Dong,Li, Linna,Feng, Hairong,Sun, Hua,Almeida-Veloso, Fabrice,Charavin, Marine,Yu, Peng,Désaubry, Laurent
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supporting information
p. 2775 - 2780
(2018/06/27)
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- Selective Carbonyl?C(sp3) Bond Cleavage To Construct Ynamides, Ynoates, and Ynones by Photoredox Catalysis
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Carbon–carbon bond cleavage/functionalization is synthetically valuable, and selective carbonyl?C(sp3) bond cleavage/alkynylation presents a new perspective in constructing ynamides, ynoates, and ynones. Reported here is the first alkoxyl-radical-enabled carbonyl?C(sp3) bond cleavage/alkynylation reaction by photoredox catalysis. The use of novel cyclic iodine(III) reagents are essential for β-carbonyl alkoxyl radical generation from β-carbonyl alcohols, including alcohols with high redox potential (EoxP>2.2 V vs. SCE in MeCN). β-Amide, β-ester, and β-ketone alcohols yield ynamides, ynoates, and ynones, respectively, for the first time, with excellent regio- and chemoselectivity under mild reaction conditions.
- Jia, Kunfang,Pan, Yue,Chen, Yiyun
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supporting information
p. 2478 - 2481
(2017/02/23)
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- Enantioselective Construction of 3-Hydroxypiperidine Scaffolds by Sequential Action of Light and Rhodium upon N-Allylglyoxylamides
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3-Hydroxypiperidine scaffolds were enantioselectively constructed in an atom-economical way by sequential action of light and rhodium upon N-allylglyoxylamides. In a formal sense, the allylic C-H bond was selectively cleaved and enantioselectively added a
- Ishida, Naoki,Ne?as, David,Masuda, Yusuke,Murakami, Masahiro
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supporting information
p. 7418 - 7421
(2015/06/30)
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- A temporary-bridge strategy for enantioselective organocatalyzed synthesis of aza-seven-membered rings
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We report the first enantioselective organocatalyzed domino synthesis of azepane moieties. This temporary-bridge strategy is based on a conceptually original annulation of ambident electrophilic and 1,4-bis-nucleophilic α-ketoamides with 1,3-bis-electrophilic enals. The obtained oxygen-bridged azepanes can be selectively transformed into optically active azepanone, azepanol or azepanedione derivatives of high synthetic value. This journal is
- Goudedranche, Sbastien,Pierrot, David,Constantieux, Thierry,Bonne, Damien,Rodriguez, Jean
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supporting information
p. 15605 - 15608
(2015/01/08)
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- A palladium(II)-catalyzed synthesis of α-ketoamides via chemoselective aroyl addition to cyanamides
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An acyl moiety generated from α-oxocarboxylic acids via decarboxylation undergoes a palladium-catalyzed chemoselective insertion into organic cyanamides to afford N-monosubstituted α-ketoamides.
- Guin, Srimanta,Rout, Saroj Kumar,Gogoi, Anupal,Ali, Wajid,Patel, Bhisma K.
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p. 2559 - 2565
(2014/09/29)
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- Oxygen-involved oxidative deacetylation of α-substituted β-acetyl amides - Synthesis of α-Keto amides
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α-Substituted β-acetyl amides could undergo C-C bond cleavage to form α-keto amides when treated with copper(II) chloride (CuCl 2) and boron trifluoride diethyl etherate (BF3× OEt2) under an oxygen atmosphere. The yield can be increased by the addition of tert-butyl hydroperoxide which alone can also effect the reaction. The reaction provides a new protocol for the synthesis of α-keto amides. Copyright
- Li, Dianjun,Yu, Wei
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supporting information
p. 3708 - 3714
(2014/01/06)
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- Superacid-promoted reactions of α-ketoamides and related systems
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(Chemical Equation Presented) The superacid-promoted reactions of α-hydroxy and α-ketoamides have been studied. Ionization of these compounds leads to varied aryl-substituted oxyindole products. In some cases, electrocyclization can lead to substituted fl
- Sai, Kiran Kumar Solingapuram,Esteves, Pierre M.,Da Penha, Eduardo Tanoue,Klumpp, Douglas A.
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p. 6506 - 6512
(2008/12/22)
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- Regio- and stereochemical aspects in synthesis of 2-allyl derivatives of glycolic, mandelic and lactic acids and their iodocyclisations to 3-hydroxy-3,4-dihydrofuran-2(5H)-ones
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Glyoxalic, phenylglyoxalic and pyruvic acids 1a-c undergo regio- and diastereoselective indium mediated allylations with allyl and cinnamyl bromides and ethyl 4-bromocrotonate to provide respective 2-allyl-, 2-(1-phenylallyl)- and 2-[(1-ethoxycarbonyl)all
- Kaur, Pervinder,Singh, Palwinder,Kumar, Subodh
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p. 8231 - 8240
(2007/10/03)
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- Enantioselective hydrogenation of α-ketoamides over Pt/A12O3 modified by cinchona alkaloids
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Pyruvamide and its N-alkylated derivatives have been synthesised and hydrogenated enantioselectively to the corresponding alcohols over an alumina-supported Pt catalyst chirally modified by adsorbed cinchonidine. Depending on the substrate structure and r
- Wang,Mallat,Baiker
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p. 2133 - 2140
(2007/10/03)
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- Synthesis of propargylic alcohols and biological effects on Echinococcus multilocularis metacestodes
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This study describes the synthesis of propargylic alcohols derived from isatin and their biochemical and morphological effects on Echinococcus multilocularis metacestodes in Meriones unguiculatus. Propargylic alcohols decreased the alkaline phosphatase and the lactate dehydrogenase activities of the metacestode selectively. The most effective compound, 1b, decreased the lactate dehydrogenase enzymatic activity, and the glucose concentration in the parasite increased, whereas the glycogen content was partially decreased. Furthermore, the ultrastructure study revealed several damages. The host-parasite relationships are very important in the intrahepatic cestodes as shown by the biochemical side effects observed in the host's liver during the treatment. An in vitro enzymatic study was performed with alcohols 1b and 1c.
- Sarciron,Audin,Delabre,Gabrion,Petavy,Paris
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p. 605 - 609
(2007/10/02)
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- In vivo and in vitro effects of methacrylanilides and acetylcarboxanilide on alkaline phosphatase activity of Echinococcus multilocularis metacestodes
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In our search for effective chemotherapy of alveolar hydatid disease we are investigating key enzymes of Echinococcus multilocularis metacestodes.Isatin (2,3-indolinedione) is well known as an inhibitor of alkaline phosphatase activity, and has been previously investigated.Acetylcarboxanilide, an "open drug" of isatin and 2 methacrylanilides were evaluated for their ability to inhibit alkaline phosphatase activity of Echinococcus multilocularis metacestodes in vivo.These "open drugs" are more efficient than isatin, and para-chloromethacrylanilide exhibits a strongselectivity for the parasite enzyme and is also effective in vitro.The results obtained with para-chloromethacrylanilide are promising.Echinococcus multilocularis / alkaline phosphatase / synthetic inhibitors /anilides
- Audin, P,Sarciron, ME,Paris, J,Petavy, AF
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p. 285 - 289
(2007/10/02)
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- Phosphoenolpyruvamides. Amide-Phosphate Interactions in Analogues of Phosphoenolpyruvate
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Ethyl esters of nitrogen-substituted carboxamides of phosphoenolpyruvate (1 and 2) were obtained from the reactions of triethyl phosphite with the corresponding nitrogen-substituted 3-bromopyruvamide.The hydrolysis of the ethyl ester portions of 1 and 2 occurs with an observed first-order rate constant that is 4 orders of magnitude larger than is estimated for triethyl phosphate under comparable conditions, indicating that participation by the neighboring carboxamide group is occurring.However, the enol phosphate ester substituent is cleaved much more slowly than are vinyl phosphate esters.The results are consistent with a mechanism in which the amide adds to the adjacent phosphate to form a reactive cyclic intermediate.The data support the proposal that amides can become phosphorylated during process that involve interactions of peptides and nucleotides or during phosphate-transfer process.The hydrolysis products of 1 and 2 may also be useful analogues of phosphoenolpyruvate in studies of enzyme mechanisms and in the design of inhibitors.
- Kluger, Ronald,Chow, Jane Frances,Croke, James J.
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p. 4017 - 4020
(2007/10/02)
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