Preparation of diethyl malonate adducts from chalcone analogs containing a thienyl ring

Nine chalcone-diethyl malonate derivatives (4a-i) were prepared by the reaction of chalcone derivatives (3a-i) with diethyl malonate in the presence of a catalytic amount of KOt-Bu in CH2CI2 in good to excellent yields. The products were characterized by FTIR, 1H-NMR, 13C-NMR and elemental analyses. KEY WORDS: Michael addition, Chalcone, KOt-Bu, Diethyl malonate  Bull. Chem. Soc. Ethiop. 2010, 24(1), 85-91. 

FREE RADICAL POLYMERIZATION OF NOVEL COPOLYMER; ETHYLENE-CO-DIETHYL METHYLENE MALONATE COPOLYMERS

Ethylene copolymers are widely used as packaging materials, adhesives and specialty polymers for well-regarded cost savings, durability, chemical resistance, and hot melt character. This work examines the use of diester monomers known as malonates to determine the plausibility of utilizing an uncommon monomer class for producing novel ethylene copolymers. Ethylene is copolymerized with diethyl methylene malonate—a simple malonate representative of more complex and highly modified malonate monomers and macromers—to produce ethylene-co-diethyl methylene malonate in a range of molecular weights. Ethylene-co-diethyl methylene malonate is analyzed to determine physical properties such as glass transition temperature, chain length and monomer incorporation. Successful copolymerization occurred under a range of temperatures and pressures in tetrahydrofuran, diethyl carbonate, and dimethyl carbonate. The produced polymers were found to have a molecular weight of 15-46 kg/mol, a glass transition temperature of 7°C, a melting temperature of 108°C, and a cold crystallization temperature of 64°C. The high concentration of a radical source inhibitor in the diethyl methylene malonate monomer solution negatively impacted molecular weight and ethylene incorporation

Preparation of Some New Substituted 5-(2\u27 -Furfuryl)-barbituric and -thiobarbituric Acids

Starting with diethyl (2-furfuryl) -malonate, obtained by reduction of diethyl (2-furfurylidene) -malonate with aluminum amalgam in wet ether, several new or hitherto insufficiently characterized 1- or/and 5-substituted 5-(2-furfuryl) -barbituric and -thiobarbituric acids, have been prepared

Crystal structure and identification of resonance forms of diethyl 2-(3-oxoiso-1,3-dihydrobenzofuran-1-ylidene)malonate

The research leading to these results received funding from the European Community's Seventh Framework Programme ([FP7/2007–2013]) under grant agreement No. 607411 (MC-ITN EREAN: European Rare Earth Magnet Recycling Network).The reaction of diethyl malonate with phthaloyl chloride in acetonitrile in the presence of triethylamine and magnesium chloride results in the formation of the title compound, diethyl 2-(3-oxo-1,3-dihydro-2-benzofuran-1-ylidene)propanedioate, C15H14O6. One of the ester groups of the diethyl malonate fragment is almost coplanar with the isobenzofuran unit, while the plane of the other group is perpendicular to it [dihedral angles = 5.45(3) and 83.30(3)°, respectively]. The C—C and C—O distances both in the heterocyclic furan ring and the diethyl malonate fragment are indicative of the dipolar delocalization occurring within the isobenzofuran unit. This delocalization is likely to be responsible for the unusual intermolecular O···O contact [2.756(2)Å], established between the O atom of the furan ring and the carbonyl O atom of the diethyl malonate fragment. In the crystal, weak C—H···O interactions are observed, which link the molecules into [100] chains.Publisher PDFPeer reviewe

Synthesis of novel β-aminocyclobutanecarboxylic acid derivatives by a solvent-free aza-Michael addition and subsequent ring closure

Novel beta-aminocyclobutanecarboxylic acid derivatives were prepared via a sequential solvent-free aza-Michael addition of benzophenone imine across 3-halopropylidenemalonates and base-induced ring closure. These highly substituted cyclobutanedicarboxylic acid derivatives were subjected to a reactivity study which demonstrated the tendency of these donor-acceptor substituted four-membered rings to be converted into their corresponding ring-opened products

Ferrocene Compounds. XXVIII. Synthesis of 2-(Ferrocenylalkyl)- and 2-[Ferrocenyl(phenyl)alkyl]-1,3-propanediols and Their Acetates

Reaction of the appropriate reagent Fc(CH2)nCHRX (1-3, 6, and 9) with sodium salt of diethyl malonate in dry xylene gave 81-91% of the corresponding diethyl (ferrocenylalkyl)malonate or diethyl ferrocenyl(phenyl)alkylmalonate (11). Using Fc(CH2)nCHRX (4, 7, 8 and 10) under similar reaction conditions, transesterification products - ethyl ferrocenylalkyl malonates or ethyl ferrocenyl(phenyl)-alkyl malonates (12) were obtained. Reduction of condensation Products 11 with lithium aluminium hydride in diethyl ether gave the corresponding diols 13 (45-66%), which will be in further studies subjected to lipase-mediated transformations with vinyl acetate to chiral monoacetates. By the action of acetic anhydride on diols 13 in a benzene solution, the corresponding mono- 14 (25-52%) and diacetates 15 (36-51%) were obtained

One-pot synthesis of 2,3-bis-(4-hydroxy-2-oxo-1,2-dihydroquinolin-3-yl)succinates and arylmethylene-bis-3,3-quinoline-2-ones

In this investigation an efficient synthesis of 2,3-bis-(4-hydroxy-2-oxo-1,2-dihydroquinolin-3-yl)succinic acid derivatives was achieved by one-pot reaction of one equivalent of aromatic amines with two equivalents of diethyl malonate in diphenyl ether and catalyzed with triethylamine. In case of applying the previous condition with aromatic amines and diethyl malonate in a ratio of 2:1, no quinolone structure was obtained, whereas N-1,N-3-bis(4-bromophenyl)malonamide, as an example, was obtained in 95% yield. Under the same previous condition, arylmethylene-bis-3,3-quinoline-2-ones were in one pot synthesized via the reaction of equal equivalents of aromatic amines and diethyl malonate together with half equivalent of the corresponding aromatic aldehydes. The structure of the obtained compounds was proved by IR, NMR and mass spectra and X-ray structure analyses. [GRAPHICS] .Peer reviewe

Reactivity of vanadium oxytrichloride with [beta]-diketones and diesters as precursors for vanadium nitride and carbide

Vanadium(V) oxytrichloride was reacted with 2,4-pentanedione, diethyl malonate, and diethyl succinate under inert conditions, forming compounds: dichloro(oxo)(2,4-pentanedione) vanadium(V) [1], dichloro(oxo)(diethyl malonate) vanadium(IV) [2] and dichloro(oxo)(diethyl succinate) vanadium(IV) [3]. Compounds 1–3 are coordinated to the vanadium centre through the two carbonyl oxygen atoms of the bidentate ligand. It was determined by X-ray crystallography that the structures of the resulting complexes were significantly different, resulting in a monomeric complex (1), a tetrameric ring (2) and a 1D coordination polymer (3). Following the synthesis and isolation of 1–3, they were tested as precursors for vanadium nitride and vanadium carbide by annealing under nitrogen and argon respectively at 1200 °C for 24 h. The resulting materials were characterised by: XRD, EDS, XPS and TEM

The degradation of L-lysine in guinea pig liver homogenate: formation of alpha-aminoadipic acid

A summary of the little that is known of the metabolism of lysine in animals is as follows: it is indispensable in the diet, its α-amino group does not participate in reversible transamination reaction in vivo (2), neither the L nor D form is attacked by the appropriate amino acid oxidase, certain ε-nitrogen-substituted derivatives can replace lysine in the diet and their α-amino groups are oxidized by amino acid oxidases (3, 4), no α-nitrogen-substituted derivatives yet prepared can substitute for lysine in the diet (4-6)

Ferrocene Compounds. XXI. Synthesis of Some β-Aryl-β-ferrocenylpropionic Acids and β,β-(1 ,1\u27-Ferrocenylene)bis(β-arylpropionic Acids)

Reaction of several a-substituted ferrocenylmethanols 1 with diethyl malonate gave condensation products 3, which were hydrolized and decar- boxylated to p-ferrocenylbutyric acid (6a) and p-aryl-p-ferrocenylpropionic acids (6b-6e). Similarly, starting from a,a\u27-disubstituted l,l\u27-ferrocenylene- bismethanols 2 p,p-(l,l\u27-ferrocenylene)bis(butyric acid) (11a) and P,P-(1,1\u27- ferrocenylene)bis(p-arylpropionic acids) (llb-lle) have been obtained via 8 and 9. The mechanism of these condensation reactions which includes transesterification of diethyl malonate with carbinols 1 and 2 has been proposed