15971-92-3Relevant academic research and scientific papers
A Selective Method for the Direct Conversion of Aldehydes into β-Keto Esters with Ethyl Diazoacetate Catalyzed by Tin(II) Chloride
Holmquist, Christopher R.,Roskamp, Eric J.
, p. 3258 - 3260 (1989)
Aldehydes are efficiently converted into β-keto esters by the addition of ethyl diazoacetate in the presence of tin(II) chloride.
Niobium(V) chloride-catalyzed C-H insertion reactions of α-diazoesters: Synthesis of β-keto esters
Yadav,Subba Reddy,Eeshwaraiah,Reddy
, p. 875 - 878 (2005)
Aldehydes react readily with ethyl diazoacetate in the presence of 5 mol% of NbCl5 in dichloromethane to produce the corresponding β-keto esters in good yields with high selectivity. This method is very useful for the preparation of β-keto esters from both electron-rich as well as electron-deficient aromatic aldehydes under mild reaction conditions.
Continuous flow synthesis of toxic ethyl diazoacetate for utilization in an integrated microfluidic system
Maurya, Ram Awatar,Min, Kyoung-Ik,Kim, Dong-Pyo
, p. 116 - 120 (2014)
An integrated microfluidic system for multiple reactions and separations of hazardous ethyl diazoacetate is presented. The integrated techniques include: a droplet technique for liquid-liquid and/or gas-liquid separation and in situ generation of the toxic reagent, a dual channel membrane technique based on a cheap polymeric microseparator for liquid-liquid separation, and a capillary microreactor for carrying out cascade reactions in a sequential and continuous manner.
Amide/Ester Cross-Coupling via C-N/C-H Bond Cleavage: Synthesis of β-Ketoesters
Chen, Jiajia,Joseph, Devaneyan,Xia, Yuanzhi,Lee, Sunwoo
, p. 5943 - 5953 (2021/04/02)
Activated primary, secondary, and tertiary amides were coupled with enolizable esters in the presence of LiHMDS to obtain good yields of β-ketoesters at room temperature. Notably, this protocol provides an efficient, mild, and high chemoselectivity method
Toward Continuous-Flow Synthesis of Biologically Interesting Pyrazole Derivatives
Das, Amrita,Ishitani, Haruro,Kobayashi, Shū
supporting information, p. 5127 - 5132 (2019/11/13)
A two-step continuous-flow synthesis of substituted pyrazole derivatives has been developed via the formation of vinylidene keto esters as key intermediates. Heterogeneous Ni2+-montmorillonite was found to be an efficient catalyst for orthoester condensation of 1,3-dicarbonyls under flow conditions. The intermediate reacted with methylhydrazine to afford pyrazole derivatives, for which suitable selection of a solvent played a key role in achieving high yields and excellent regioselectivities of the desired products. An application of this protocol has been demonstrated by the synthesis of a key intermediate for biologically active pyrazoles such as Bixafen. (Figure presented.).
Pyrazole alcohol compound, pharmaceutical composition thereof and application thereof to drugs
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Paragraph 0128; 0131, (2018/10/19)
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.
The synthesis of pyrroles and oxazoles based on gold α-imino carbene complexes
Loy, Nicole S. Y.,Choi, Subin,Kim, Sunggak,Park, Cheol-Min
supporting information, p. 7336 - 7339 (2016/06/14)
Cationic gold complexes of α-oximimino carbenes have been identified to react with weak nucleophiles including enol ethers and nitriles. These findings allowed us to develop the highly efficient synthesis of pyrroles and oxazoles.
Synthesis of the 1,3,4-Oxadiazole Core through Thermolysis of Geminal Diazides
Erhardt, Hellmuth,Mohr, Fabian,Kirsch, Stefan F.
supporting information, p. 5629 - 5632 (2016/12/14)
The thermolysis of geminal diazides derived from acylacetate compounds is an efficient tool for the rapid construction of the 1,3,4-oxadiazole core. While a broad range of ethyl esters undergoes smooth transformation to the desired heterocycles that contain the ester moiety in moderate to high yields, the analogous tert-butyl esters give rise to the oxadiazoles with acyl groups, presumably through a pathway of decarboxylation followed by a new acyl transfer.
Synthesis and biological evaluation of pyrazolo[3,4-b]pyridin-4-ones as a new class of topoisomerase II inhibitors
Tabrizi, Mojgan Aghazadeh,Baraldi, Pier Giovanni,Baraldi, Stefania,Prencipe, Filippo,Preti, Delia,Saponaro, Giulia,Romagnoli, Romeo,Gessi, Stefania,Merighi, Stefania,Stefanelli, Angela,Fazzi, Debora,Borea, Pier Andrea,Maia, Rodolfo Couto,Romeiro, Nelilma C.,Fraga, Carlos A.M.,Barreiro, Eliezer J.
, p. 342 - 353 (2016/10/11)
A series of 1,3,6-triphenylpyrazolo[3,4-b]pyridin-4-one derivatives was designed, synthesized and evaluated for cytotoxic activity in A375 human melanoma and human erythroleukemia (HEL) cells. The new pyrazolopyridones displayed comparable activities to the antitumor compound etoposide. The inhibitory effect of compounds 17, 18, 27 and 32 against topoisomerase II-mediated cleavage activities was measured finding good correlation with the results obtained from MTS assay. Docking studies into bacterial topoisomerase II (DNA Gyrase), topoisomerase IIα and topoisomerase IIβ binding sites in the DNA binding interface were performed.
Enantioselective Mannich reaction of β-keto esters with aromatic and aliphatic imines using a cooperatively assisted bifunctional catalyst
Neuvonen, Antti J.,Pihko, Petri M.
supporting information, p. 5152 - 5155 (2015/01/08)
An efficient urea-enhanced thiourea catalyst enables the enantioselective Mannich reaction between β-keto esters and N-Boc-protected imines under mild conditions and minimal catalyst loading (1-3 mol %). Aliphatic and aromatic substituents are tolerated on both reaction partners, affording the products in good enantiomeric purity. The corresponding β-amino ketones can readily be accessed via decarboxylation without loss of enantiomeric purity.
