3097-74-3Relevant academic research and scientific papers
A one-step radical synthesis of pyrrol-2-acetic acids
Byers, Jeffrey H.,Duff, Michael P.,Woo, Gregory W.
, p. 6853 - 6855 (2003)
Pyrrol-2-acetic acids were generated following a procedure involving I-transfer radical addition of iodoacetic acids to pyrrole with spontaneous loss of HI. This procedure also allows for efficient syntheses of 2-alkyl pyrroles through subsequent thermolytic decarboxylation.
Preparation of mono-substituted malonic acid half oxyesters (SMAHOs)
Condon, Sylvie,Le Gall, Erwan,Pichon, Christophe,Presset, Marc,Xavier, Tania
supporting information, p. 2085 - 2094 (2021/09/02)
The use of mono-substituted malonic acid half oxyesters (SMAHOs) has been hampered by the sporadic references describing their preparation. An evaluation of different approaches has been achieved, allowing to define the best strategies to introduce diversity on both the malonic position and the ester function. A classical alkylation step of a malonate by an alkyl halide followed by a monosaponification gave access to reagents bearing different substituents at the malonic position, including functionalized derivatives. On the other hand, the development of a monoesterification step of a substituted malonic acid derivative proved to be the best entry for diversity at the ester function, rather than the use of an intermediate Meldrum acid. Both these transformations are characterized by their simplicity and efficiency, allowing a straightforward access to SMAHOs from cheap starting materials.
Decarboxylative Mannich Reactions with Substituted Malonic Acid Half-Oxyesters
Xavier, Tania,Condon, Sylvie,Pichon, Christophe,Le Gall, Erwan,Presset, Marc
, p. 5452 - 5462 (2021/05/07)
The decarboxylative Mannich reaction between imines and substituted malonic acids half-oxyesters (SMAHOs) has been developed using 1,4-diazabicyclo[2.2.2]octane (DABCO) as an organocatalyst. The reaction proceeds under simple reaction conditions and toler
Enantioselective α-Amination of Acyclic 1,3-Dicarbonyls Catalyzed by N-Heterocyclic Carbene
Santra, Surojit,Maji, Ujjwal,Guin, Joyram
supporting information, p. 468 - 473 (2020/02/04)
Herein, we describe a method for the catalytic enantioselective α-amination of α-substituted acyclic 1,3-ketoamides and 1,3-amidoesters that affords the products possessing N-substituted quaternary stereocenters with a chiral N-heterocyclic carbene (NHC). The reaction is based on the utilization of an intrinsic Br?nsted base characteristic of NHC that enables the catalytic formation of a chiral ion pair comprising the enolate and the azolium ion. A series of challenging open-chain α-substituted 1,3-dicarbonyls are aminated via this method with ee's of ≤99%.
Synthesis of α,β-Disubstituted Acrylates via Galat Reaction
Xavier, Tania,Condon, Sylvie,Pichon, Christophe,Le Gall, Erwan,Presset, Marc
supporting information, p. 6135 - 6139 (2019/08/28)
Galat reactions between aldehydes and substituted malonic acids half oxyester were found to be efficiently catalyzed by morpholine in refluxing toluene. This transformation allows the stereoselective synthesis of diverse α,β-disubstituted acrylates in moderate to good yields. This method constitutes an attractive alternative to existing methods in terms of scope and eco-compatibility.
Ester derivative industrial production process
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Paragraph 0054; 0055; 0056; 0057, (2016/10/10)
The present invention provides an ester derivative industrial production process which is characterized in that a monoester or a diester derivative is obtained by reaction of a compound A and carbon monoxide or carbon dioxide under the effect of a catalyst; the production process is simple, and is different from complex production ways and demanding production conditions in the prior art, and the target ester derivative product can be synthesized by one step. The production process and synthetic routes are optimized, so that the production process is fewer in side effects, convenient in post treatment, mild in production conditions, and suitable for industrial production modes.
NOVEL PIPERAZINE DERIVATIVES AS INHIBITORS OF STEAROYL-CoA DESATURASE
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Page/Page column 35, (2009/10/01)
The present invention relates to piperazine derivatives that act as inhibitors of stearoyl-CoA desaturase. The invention also relates to methods of preparing the compounds, compositions containing the compounds, and to methods of treatment using the compounds.
Highly efficient selective monohydrolysis of dialkyl malonates and their derivatives
Niwayama, Satomi,Cho, Hanjoung,Lin, Chunlei
, p. 4434 - 4436 (2008/12/21)
The highly efficient selective monohydrolysis of symmetric diesters has been applied to monohydrolysis of several dialkyl malonates and their derivatives. The best conditions apply 0.8-1.2 equiv of aqueous KOH with a co-solvent, THF or acetonitrile, at 0 °C. The procedure is highly practical, yielding the corresponding half-esters in high yields in a straightforward manner, without inducing decarboxylation. It was found that the selectivity tends to become higher with increased hydrophobicity.
SYNTHESIS OF HALF ESTERS
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Page/Page column 17-21; 23, (2009/01/24)
A method for hydrolyzing an ester is provided. In accordance with the method, a compound A is provided which has first and second ester moieties. The compound is reacted in a liquid medium with a base having the formula MaXb,such that the first ester moiety is converted to a carboxyl moiety and the second ester moiety remains, wherein the ratio [Xk-]:[A] in the liquid medium is no greater than 1.6, and wherein k > 0.
Selective monoesterification of malonic acid catalyzed by boric acid
Levonis, Stephan M.,Bornaghi, Laurent F.,Houston, Todd A.
, p. 821 - 823 (2008/03/12)
Boric acid catalyzes the monoesterification of malonic acid, likely through a chelation mechanism that is not available to the monoester product. Under more forcing conditions, diesters form to some extent, but conditions can be optimized to favour the monoester product (56?80%). With the easily handled solid acid catalyst, these reactions can be run with excess alcohol as solvent or with stoichiometric amounts of alcohol in acetonitrile with moderate heating. CSIRO 2007.
