Acrylic Acid Derivatives Research Articles

A cascade reaction sequence en route to 7-substituted 2-aminopyrrolo[1,2- a]pyrimidine-4,6-diones and the corresponding acrylic acid derivatives

Reaction of α-bromo ketones with 6-amino-2-methylpyrimidin-4(3 H)-one under basic conditions and in the presence of atmospheric oxygen affords novel 7-substituted 2-amino-pyrrolo[1,2- a]pyrimidine-4,6-diones that are readily hydrolyzed to afford the corresponding acrylic acid derivatives. The reaction sequence consists of an initial alkylation, followed by an unexpected condensation, elimination, and oxidation sequence to afford the products. This cascade reaction sequence represents a rapid and unprecedented route to the described small molecules.

Synthesis of 2-(9-Fluorenyl)acrylic Acid Derivatives via Intramolecular Friedel-Crafts Reaction of Morita-Baylis-Hillman Adducts of 2-Biphenyl­carboxaldehydes

Treatment of propiolic acid esters or N,N-dimethylpropynamide and various 2-biphenylcarboxaldehydes with tetrabutyl­ammonium iodide/zirconium(IV) chloride, titanium(IV) chloride/dimethyl sulfide, or titanium(IV) bromide/dimethyl sulfide or treatment of methyl acrylate and 2-biphenylcarboxaldehydes with 1,4-diazabicyclo[2.2.2]octane (DABCO) and triethanolamine induce an aldol-type reaction to furnish β-halo-α-(hydroxymethyl)acrylates or α-(hydroxymethyl)acrylates, respectively. These can be used for the preparation of 2-(9H-fluoren-9-yl)acrylic acid derivatives by intramolecular Friedel-Crafts reaction with sulfuric acid in tetrachloromethane.

Photoinduced Diastereoselective Addition of Perfluoroalkyl Iodides to Acrylic Acid Derivatives for the Synthesis of Fluorinated Amino Acids

Photoinduced diastereoselective addition of perfluoroalkyl iodides in the presence of an aqueous solution of Na2S2O3 was an excellent method for iodoperfluoroalkylation of acrylic acid derivatives bearing a chiral auxiliary, with moderate to good stereoselectivities and with no detectable side products. The iodoperfluoroalkylation of N-acyloylcamphorsultam provided a convenient route for preparing chiral fluorine-containing amino acids.

A platform for designing HIV integrase inhibitors. Part 1: 2-Hydroxy-3-heteroaryl acrylic acid derivatives as novel HIV integrase inhibitor and modeling of hydrophilic and hydrophobic pharmacophores

We present a novel series of HIV integrase inhibitors, showing IC 50s ranging from 0.01 to over 370 μM in an enzymatic assay. Furthermore, pharmacophore modeling study for the inhibitors was carried out to elucidate the structure–activity relationships. Finally, we found a 3D-pharmacophore model, which is composed of a hydrophilic and a hydrophobic domain, providing valuable information for designing other novel types of integrase inhibitors.

Synthesis and properties of polyvinyl chloride films with modified surface

Atomic-force microscopy was used to study structural chemical transformations on the surface of polyvinyl chloride films subjected to modification with compounds based on acrylic acid derivatives, with preliminary activation of the polymer surface with a corona discharge.

Investigation into the influence of organic modifiers and ultradispersed hybrid fillers on the structure and properties of glass-ceramic coatings prepared by the sol-gel method

Glass-ceramic coatings on nickel and its alloys are produced from organic-inorganic hybrids by the sol-gel method. The coatings are applied using sol-gel systems composed of tetraethoxysilane (inorganic dopant), as well as of finely dispersed oxide and ultradispersed hybrid fillers. Acrylic and methacrylic acid derivatives are taken as organic modifiers. Oligocarbonate dimethacrylate-substituted tetranuclear titanium oxide clusters are used as the ultradispersed hybrid filler. The influence of the organic modifiers and ultradispersed hybrid fillers on the physicochemical processes occurring in the sol-gel systems and on the electrical parameters of the coatings are experimentally studied, and the data obtained are analyzed.

Stereospecific Synthesis of New 4‐Amino‐1,2,3‐cyclohexanetricarboxylic Acids and 4‐Amino‐1,3‐cyclohexanedicarboxylic Acids.

AbstractFor Abstract see ChemInform Abstract in Full Text.

Design and synthesis of low molecular weight compounds with complement inhibition activity

An attempt was made to synthesize a series of non-cytotoxic low molecular weight compounds of varying substitutions and functionalities having pharmacophore activity like carbonyl compounds, carboxylic acid and bioisosteres like tetrazole and phenyl acrylic acid. The in vitro assay of these analogues for the inhibition of complement activity revealed significant inhibitory activity for varying substituents and, particularly, for bioisosteres, that is, tetrazole and phenyl acrylic acid derivatives.

Synthesis and Biological Activity of New Derivatives of 3-(3,4-Diaryl-1,2,4-triazole-5-yl)propenoic Acid.

Abstract New 3-(3,4-diaryl-1,2,4-triazole-5-yl)propenoic acid derivatives (8–14) were synthesized by condensation of N3-substituted amidrazones (1–7) with maleic anhydride. Molecular structure of obtained compounds was confirmed by an elemental analysis, IR and 1H NMR spectra, and the X-ray crystallography for compound 11. The influence of the compound 9 on the central nervous system (CNS) of mice in some behavioural test was examined. The investigated compound showed anticonvulsive activity and potent antinociceptive action.

Stereospecific Synthesis of New 4-Amino-1,2,3-cyclohexanetricarboxylic Acids and 4-Amino-1,3-cyclohexanedicarboxylic Acids

Diels-Alder adducts of 1,2-dihydropyridine with maleic and acrylic acid derivatives were stereospecifically converted by way of RuO4 oxidation into new 4-amino-1,2,3-cyclohexanetricarboxylic acids and 4-amino-1,3-cyclohexanedicarboxylic acids.

Synthesis and biological activity of new derivatives of 3-(3,4-diaryl-1,2,4-triazole-5-yl)propenoic acid

New 3-(3,4-diaryl-1,2,4-triazole-5-yl)propenoic acid derivatives (8–14) were synthesized by condensation of N 3-substituted amidrazones (1–7) with maleic anhydride. Molecular structure of obtained compounds was confirmed by an elemental analysis, IR and 1H NMR spectra, and the X-ray crystallography for compound 11. The influence of the compound 9 on the central nervous system (CNS) of mice in some behavioural test was examined. The investigated compound showed anticonvulsive activity and potent antinociceptive action.

Modular chiral ligands: the profiling of the Mandyphos and Taniaphos ligand families

A set of 11 ferrocenyl based diphosphine ligands (eight Mandyphos and three Taniaphos) was tested in more than 150 experiments using 20 test reactions. For the assessment of new ligands, a two-pronged strategy was developed consisting of a basic and an extended profiling. The basic profiling showed that the choice of the substituents at the P atoms has a significant effect on the catalyst performance. In the extended profiling it was confirmed that the Mandyphos ligands, in particular M4 with two bis(3,5-dimethyl-4-methoxyphenyl)phosphino groups, and the Taniaphos ligands, especially the all-phenyl derivative T1, showed good to outstanding performances in the hydrogenation of selected α- and β-enamides, acrylic acid derivatives, itaconates, β-ketoesters and 1,3-diketones yielding the corresponding products with up to 99% ee and at substrate/catalyst ratios up to 25,000.

Synthesis of polymer gel with chiral helical cavity by molecular imprinting using bifunctional vinyl monomers

The molecular imprinting method was applied for synthesizing gels with a chiral helical cavity using various bifunctional vinyl monomers, such as α-(benzyloxymethyl)acrylic acid derivatives as a monomer, and one-handed helical (+)-poly(diphenyl-2-pyridylmethyl methacrylate) as a template. The chiral gels were almost quantitatively prepared after removal of the template polymer by hydrolysis of the ester groups. The obtained gels exhibited chiral resolution powers toward various racemates, such as trans-stilbene oxide and Tröger's base, and the substituents on the phenyl group of the monomer significantly affected the recognition ability. The observed separation factors were higher than those of the gels prepared from the mono-functional vinyl monomer, methacrylic acid.

Stereospecific Synthesis of New 2,3,4,5‐Piperidinetetracarboxylic Acids and 2,3,5‐Piperidinetricarboxylic Acids.

AbstractFor Abstract see ChemInform Abstract in Full Text.

Stereoselectivity in 1,3‐Dipolar Cycloaddition Reactions of 2‐Benzopyrylium‐4‐olate with Acrylic Acid Derivatives Catalyzed by Rare Earth Metal Triflates.

AbstractFor Abstract see ChemInform Abstract in Full Text.

Stereospecific synthesis of new 2,3,4,5-piperidinetetracarboxylic acids and 2,3,5-piperidinetricarboxylic acids

Diels–Alder adducts of 1,2-dihydropyridine with maleic and acrylic acid derivatives were stereospecifically converted by way of RuO4 oxidation into new r-2,c-3,c-4,c-5-piperidinetetracarboxylic acid, r-2,t-3,t-4,c-5-piperidinetetracarboxylic acid, r-2,c-3,c-5-piperidinetricarboxylic acid, and r-2,t-3,c-5-piperidinetricarboxylic acid.

Unusual fragmentation of fulvene endoperoxides with phenyliodosyl bis(trifluoroacetate) (PIFA)

AbstractReaction of unsaturated fulvene endoperoxides with dimethyl 1,2,4,5‐tetrazine‐3,6‐dicarboxylate gave saturated fulvene endoperoxides containing the 1,2‐dihydropyridazine ring. Treatment of dihydropyridazine endoperoxides with water followed by phenyliodosyl bis(trifluoroacetate) oxidation provided acrylic acid derivatives and dimethyl pyridazine‐3,6‐dicarboxylate.

Interactions between Sodium Dodecyl Sulfate and Six Nonionic Copolymers Containing 10 Mol of Different Covalently Bonded Derivatives of Vinyl Acrylic Acid: Electromotive Force and Microcalorimetry Studies

The binding of sodium dodecyl sulfate (SDS) to six random nonionic copolymers with the general chemical name polyvinyl(methyl imidazole-co-pyrrolidone-co-acrylate) were studied using electromotive force measurements (EMF) and isothermal titration calorimetry (ITC). In terms of their composition expressed in mole percent, each polymer contains 45 mol % methyl vinyl imidazole (MVI), 45 mol % vinyl pyrrolidone (VP), and 10 mol % of each of six different substituted acrylates. The purpose of the work was to investigate how subtle structural changes in the acrylate monomer affect the binding properties of SDS. The results showed significant differences in the binding behavior of the polymers, which are reflected in the determination of critical constants associated with SDS binding, like binding isotherms, the degree of sodium ion association to the bound SDS micelles, and the binding enthalpies as measured by ITC, especially in the early stages of binding. This opens the possibility of using ITC and EMF exper...

Antitumour polycyclic acridines. Palladium(0) mediated syntheses of quino[4,3,2-kl]acridines bearing peripheral substituents as potential telomere maintenance inhibitors.

Pd(0) mediated couplings between substituted 2-(pivaloylamino)benzeneboronic acids and 3,6-disubstituted-10-methylacridones 13 bearing a bromo or trifluoromethylsulfonyloxy substituent in the 1-position yield intermediate 1-arylacridones 16 which can be can be cyclised to new 8-methylquino[4,3,2-kl]acridines 17 with phosphorus oxychloride or 6 M HCI in EtOH. Heck reactions between triflate-substituted substrates 17 and acrylic acid derivatives afforded quinoacridines with unsaturated side-chains in the 6-position. Alkylboranes, prepared by interaction of 9-borabicyclo[3,3,1]nonane (9-BBN) and allyl acetate or N-allyltrifluoroacetamide, participated in Suzuki-Miyaura reactions with chloro-substituted 8-methylquinoacridines to form derivatives bearing functionalised propyl groups in the 6- and 10-positions. Representative 8-methylquinoacridines were methylated with methyl iodide to yield telomerase-inhibitory 8,13-dimethylquinoacridinium iodides 24.

Efficient pi-facial control in the ene reaction of nitrosoarene, triazolinedione, and singlet oxygen with tiglic amides of the bornane-derived sultam as chiral auxiliary: an economical synthesis of enantiomerically pure nitrogen- and oxygen-functionalized acrylic acid derivatives.

The ene reaction of 4-nitronitrosobenzene (ArNO), N-phenyl-1,2,4-triazoline-3,5-dione (PTAD), and singlet oxygen (1O2) with the optically active tiglic-acid derivatives of Oppolzer's bornane-derived sultam affords the respective ene products regioselectively in excellent diastereoselectivity (de up to 99%) and in good yield (55-90%). The enophiles ArNO and PTAD give with the methyl-substituted substrate exclusively the like-configured ene adduct, while 1O2 leads to an 83:17 diastereomeric mixture. With the sterically more demanding isopropyl-substituted derivative even the smallest enophile 1O2 forms exclusively the like diastereomer. The high diastereoselectivity is rationalized in terms of the proper conformational alignment of the substrate and a preferred enophilic attack from the C(beta)-re face of the double bond. This concept offers an efficient synthetic route to enantiomerically pure nitrogen- and oxygen-functionalized acrylic acid derivatives.