73062-47-2Relevant academic research and scientific papers
Double-substituted cyano acetic acid ester compound solvent-free preparation method
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Paragraph 0018; 0040; 0041; 0043; 0046, (2019/05/11)
Double-substituted cyano acetic acid ester compound solvent-free preparation method, comprises the following steps: step one: the aromatic aldehyde with the cyano acetate, dihydro pyridine ester, [...], alkali in accordance with the molar ratio of 1: (1 - 2): (1 - 2): (1 - 3): (1 - 5) are added to a reaction in the test tube, heating up to 80 - 100 °C, stirring for 0.5 - 3 h; step two: step a product obtained using silica gel as stationary phase, petroleum ether and ethyl acetate mixture as the mobile phase to the column chromatography, the final double-substituted cyano ethyl acetate. The present invention relates to aromatic aldehyde, cyano acetic acid esters, [...], dihydro pyridine ester as the raw material, four component in the solvent-free one-pot synthesis reaction is carried out under the conditions of preparation double-substituted cyano acetic acid ethyl ester, with economic and environmental protection, high reaction efficiency, wide substrate range, synthesis is convenient and the like.
Overturning established chemoselectivities: Selective reduction of arenes over malonates and cyanoacetates by photoactivated organic electron donors
Doni, Eswararao,Mondal, Bhaskar,O'Sullivan, Steven,Tuttle, Tell,Murphy, John A.
supporting information, p. 10934 - 10937 (2013/08/23)
The prevalence of metal-based reducing reagents, including metals, metal complexes, and metal salts, has produced an empirical order of reactivity that governs our approach to chemical synthesis. However, this reactivity may be influenced by stabilization of transition states, intermediates, and products through substrate-metal bonding. This article reports that in the absence of such stabilizing interactions, established chemoselectivities can be overthrown. Thus, photoactivation of the recently developed neutral organic superelectron donor 5 selectively reduces alkyl-substituted benzene rings in the presence of activated esters and nitriles, in direct contrast to metal-based reductions, opening a new perspective on reactivity. The altered outcomes arising from the organic electron donors are attributed to selective interactions between the neutral organic donors and the arene rings of the substrates.
A gallium-catalyzed cycloisomerization/Friedel-Crafts tandem
Li, Hui-Jing,Guillot, Regis,Gandon, Vincent
supporting information; experimental part, p. 8435 - 8449 (2011/03/19)
Under noble (Au, Pt, Ru) and group 13 (Ga, In) metals catalysis, 1,6-arenynes rearrange to give 1,2-dihydronaphthalenes in a high yielding, regiocontrolled fashion. When the reaction is carried out in the presence of electron-rich arenes (anisole, phenol, indole derivatives), Friedel-Crafts addition may follow the cycloisomerization step. Only GaX3 salts proved able to catalyze these two C-C bond formation events. This specificity of gallium has been exploited for the synthesis of valuable polycyclic compounds that would be very difficult to prepare otherwise. For instance, tetrahydroisoquinolines and tetrahydrobenzoazepines have been obtained by selective 6-exo-dig or 7-endo-dig cyclization of N-tethered 1,6-arenynes. DFT calculations were carried out to shed light on the mechanism and provide a rationale for this regiodivergency. Computations also reveal the fundamental role of the tether in the stabilization of carbocationic species. Differential reactivities of other types of substrates in gallium- and gold-catalyzed cascades are also exposed, showing that the two approaches are complementary. In particular, bimolecular Friedel-Crafts additions are facilitated under gallium catalysis.
Ionic liquid as catalyst and solvent: the remarkable effect of a basic ionic liquid, [bmIm]OH on Michael addition and alkylation of active methylene compounds
Ranu, Brindaban C.,Banerjee, Subhash,Jana, Ranjan
, p. 776 - 782 (2007/10/03)
A basic ionic liquid, 1-methyl-3-butylimidazolium hydroxide, [bmIm]OH, catalyzes the Michael addition of active methylene compounds to conjugated ketones, carboxylic esters and nitriles. It further catalyzes the addition of thiols to α,β-acetylenic ketones and alkylation of 1,3-dicarbonyl and -dicyano compounds. The Michael addition to α,β-unsaturated ketones proceeds in the usual way, giving the monoaddition products, whereas addition to α,β-unsaturated esters and nitriles leads exclusively to the bis-addition products. The α,β-acetylenic ketones undergo double conjugate addition with thiols producing β-keto 1,3-dithio-derivatives. In the alkylation reaction the acyclic 1,3-diketones are monoalkylated, whereas cyclic ketones undergo dialkylation under identical conditions. All these reactions were carried out without any organic solvent. The ionic liquid can also be recycled.
Efficient preparation of α,α-dialkyl-α-(phenylselanyl) acetates and α,β-unsaturated esters from the corresponding α,α-dialkyl-α-cyanoacetates by a lithium naphthalenide induced reductive selenenylation process
Ko, Yen-Chun,Zhu, Jia-Liang
, p. 3659 - 3665 (2008/09/19)
An array of α,α-dialkyl-α-(phenylselanyl)acetates has been synthesized very efficiently from readily available α,α- dialkyl-α-cyanoacetates, by use of lithium naphthalenide induced reductive α-selenenylation as a key operation. Moreover, the selanyl esters thus generated in situ could be converted further, in a one-pot treatment with hydrogen peroxide and acetic acid, into the corresponding α,β- unsaturated esters in moderate to high yields. The C=C bond formation was highly regio- and/or diastereoselective in some cases. Georg Thieme Verlag Stuttgart.
A convenient new procedure for the construction of highly substituted acetates. Reductive alkylation of α-cyano esters
Shia, Kak-Shan,Chang, Nien-Yin,Yip, Judy,Liu, Hsing-Jang
, p. 7713 - 7716 (2007/10/03)
A convenient, highly efficient general method for the preparation of highly substituted acetates has been developed, making use of reductive alkylation of α-cyano esters as a key operation.
Alkylation of Monosubstituted Malonate Anions With Pyridinium and Quinolinium Salts
Katritzky, Alan R.,Aurrecoechea, Jose M.
, p. 342 - 345 (2007/10/02)
Monosubstituted malonate anions are alkylated at room temperature with 1-(sec-alkyl)quinolinium salts.Hindered disubstituted malonate esters can thus be prepared under very mild conditions.
