Ethylcyanoacetate

Ethylcyanoacetate (227), Rj = CH2C02Et, also reacts with ethylthio-glycolate to afford the corresponding ethyl-2-thiazolylacetate (230), R, -CH2C02Et, R2 = H, after cyclization of the acyclic intennediate in the presence of sodium acetate (542). 

Enamines can be used in place of an aldehyde or ketone in the Gewald reaction. Compound 19 reacted with ethylcyanoacetate and sulfur in the presence of morpholine to give aminothiophene 20 in good yield. ... 

When an aldehyde is used as the starting material in the Gewald reaction, a 5-alkyl-2-aminothiophene is the product isolated. For example, when 3-methylbutanal 25 was combined with ethylcyanoacetate 15 and sulfur in the presence of triethylamine, aminothiophene 26 is the only product observed in this reaction. However, when an a-tosyloxy-ketone 27 and sodium sulfide were employed in the reaction, the corresponding 4-alkyl-2-aminothiophene 28 was the sole reaction product. ... 

In its manufacture, methyl ethyl ketone is condensed with ethylcyanoacetate to give ethyl-2-cyano-3-methyl-2-pentenoate. That, in turn, adds HCN to give ethyl-2,3-dicyano-3-methyl-pentanoate. Saponification and decarboxylation gives 2-methyl-2-ethyl succinonitrile. Heating with aqueous NH3 gives the diamide which loses NHj and cyclizes to ethosuximide. 

Another method of phenobarbital synthesis starts with condensation of benzyl cyanide with diethylcarbonate in the presence of sodium ethoxide to give a-phenylcyanoacetic ester (4.1.5). Alkylation of the ester (4.1.5) using ethylbromide gives a-phenyl-a-ethylcyanoacetic... 

Rh(PNBD)- NH2-MCM41 Benzaldehyde + ethylcyanoacetate Ethyl 2-cyano-3-phenylpropionate Base + hydrogenation (85)c — 1 h under Ar + 12 h under H2 (7 bar) [4]... 

The acetophenone XXVII was condensed with ethylcyanoacetate (ammonium acetate-acetic acid catalyst) to yield the substituted acrylonitrile XXVIII. When XXVIII was heated in ethanol with... 

The synthesis of a series of pyrimido[l,2-a]benzimidazoles 98 has been reported by Dandia and co-workers [136] through a MCR of 2-aminobenzimidazole, mal-ononitrile or ethylcyanoacetate and a carbonyl compound in water. Cyclic as well as acyclic carbonyl compounds could be used. The reaction highly benefits from microwave (domestic oven) irradiation in terms of rate and the compounds 98 were obtained in good yields (Scheme 75). 

A variation of the BigineUi condensation in which aldehydes and guanidine hydrochloride were reacted with ethylcyanoacetate (Scheme 9) under basic conditions provided 2-aminopyrimidines in a one-step synthesis [29]. The products were tested against E. coli and S. aureus bacteria. Compound 40 was selectively active against S. aureus. 

Hydroxythiazole, from chloroacetaldehyde and ammonium thiocaibamate, 258 4-Hydroxy-2-thiazolecarboxylic acid ethyl ester, self condensation of, 294 synthesis of, from ethylcyanoacetate and ethylthioglycolate, 294 from thioamides and a-haloacids or esters, 294... 

In this work, we report the study of the catalytic activity of immobilized amino groups in the Knoevenagel condensation of benzaldehyde (BA) with ethylcyanoacetate (EGA) in DMSO solution (scheme 1). 

Benzaldehyde (1.75 g, 16.5 mmol.) and ethylcyanoacetate (1.87 g, 16.5 mmol.) was added to the modified catalyst (0.22 g) previously activated at 150°C under vacuum overnight and stirred in suspension in DMSO ( total volume 55 ml) under nitrogen atmosphere at 80°C. The reaction progress was... 

While oxiranes afford with sodium ethylcyanoacetate only oc-cyano-y-butyrolactone, i.e., the insertion of the hydroxyethyl moiety into ethyl cyanoacetate,6 thiiranes give with sodium cyanoacetate, in a one-step... 

The catalytic performance of the NCNT was tested via the Knoevenagel condensation of benzaldehyde (BA) with ethylcyanoacetate (ECA) to form ethyl-a-cyanocinnamate (ECC). The NCNT (1 g) were crushed, heated to 423 K under vacuum and maintained under these conditions for 1 h. The reactants, BA (0.01 mol) and ECA (0.01 mol), were dissolved in ethanol (50 mL) and carbondioxide was removed using the freeze-thaw method. The solution was then added to the NCNT and the reaction was performed under reflux conditions. To monitor the progress of the reaction, samples of the reaction mixture were taken regularly for GC analysis. 

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