- Optimal synthetic design of second-order nonlinear optical material with good temporal stability
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Second-order nonlinear optical copolymers containing p-hydroxyphenyl maleimide or 4-cinnamoyloxy-phenylmaleimide as a comonomer were newly synthesized. For improving the temporal stability, we adopted the crosslink reaction thermally and photochemically. Second-order nonlinear optical properties of the poled/cured films were investigated in terms of the second harmonic generation (SHG) and linear electro-optic (EO) coefficient measurement. SHG coefficient, d33 was found to be 14 pm/V at the fundamental wavelength of 1064 nm and EO coefficient, r33 was found to be 25-30 pm/V at 633 nm wavelength in two different crosslinked structures. To prevent the orientational relaxation of poled polymer, thermal crosslink reaction was induced using diisocyanate as a crosslinker between the side chains themselves. Another photo-crosslink was induced exposing the film at 257 nm wavelength during poling. Temporal stabilities of second-order NLO coefficients of crosslinked polymer systems were proved much better than that of guest-host system or other side chain polymers.
- Choi,Song,Jahng,Kim
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Read Online
- Comment on: Synthesis of new azo compounds based on N-(4-Hydroxyphenyl)maleimide and N-(4-Methylphenyl)maleimide. Molecules 2010, 15, 7498–7508
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The synthesis of (E)-phenylazo-3-N-(4-hydroxyphenyl)maleimide (1) using a procedure previously reported in Molecules is deemed to be erroneous. A detailed re-investigation of the earlier work suggests that the spectral data for key intermediates and the final product, (1), was mis-assigned. We conclude that compound (1) was not synthesized, but rather an unusual ring opening reaction of the maleimide unit of the starting material, N-(4-hydroxyphenyl)maleimide (2) leading to the generation of (Z)-4-((4-hydroxyphenyl)amino)-4-oxobut-2-enoic acid, (3) was observed instead. Examination of the original experimental data reveals systematic errors in the reporting of all of the combustion microanalytical data. Overall, the present investigation suggests that errors in the interpretation of spectral data, falsification of analytical data and selective editing of experimental results raise questions over the veracity of the work presented in the original paper.
- Morrison, John J.,Brandt, Viktoria K.,Yeates, Stephen G.
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Read Online
- Application of maleimide compound as chitin synthase inhibitor
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The invention discloses an application of a maleimide compound as shown in a formula I. In the formula I, R0 is phenyl, benzyl, phenethyl, phenylpropyl, p-fluorophenyl, p-chlorophenyl, p-bromophenyl,p-methoxyphenyl, p-methylphenyl or p-hydroxyphenyl, R1 is hydrogen, methyl, phenyl or chlorine; and R2 is hydrogen, methyl, phenyl or chlorine. The provided maleimide compound has a good inhibition effect on chitin synthase.
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Paragraph 0120-0123; 0136-0139
(2020/07/12)
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- New phosphorus- and nitrogen-containing poly(methyl methacrylate)-based copolymer: Enhanced flame retardancy and thermal stability
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Pure poly(methyl methacrylate) (PMMA) always exhibits high flammability and low thermal stability. To address that, a novel reactive comonomer containing phosphorus and nitrogen elements, 4-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl) phenyl diethylphosphoramidate (PDM), was successfully synthesized and then introduced into PMMA matrix through emulsion copolymerization method. The structure of PDM and as-obtained poly(MMA-co-PDM) copolymers was characterized using Fourier transform infrared (FT-IR), 1H nuclear magnetic resonance spectroscopy (1H NMR) and 31P NMR. From thermal gravimetric analysis and microscale combustion calorimeter, the poly(MMA-co-PDM) copolymers exhibit significantly enhanced flame retardancy and thermal stability, such as the higher degradation temperatures, and decreased peak heat release rate (maximally by 24.1%) and total heat release (maximally by 22.1%). The glass transition temperature (Tg) values of poly(MMA-co-PDM) copolymers obtained by differential scanning calorimetry slightly decrease as the raising flexibility of polymer chain. The char residue analysis by scanning electron microscopy and FT-IR demonstrates that the incorporation of PDM can catalyze the charring of copolymers in condensed phase and form an excellent thermal stability char residue with aromatic structure, further preventing the inner substrate from further combustion. The detailed mechanism was proposed.
- Shi, Xingxing,Jiang, Saihua,Xiao, Liang
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p. 333 - 342
(2019/06/17)
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- Monomer compound and preparation method thereof, and copolymer, preparation method and applications thereof
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The invention relates to the technical field of polymer oil displacement, and discloses a monomer compound and a preparation method thereof, and a copolymer, a preparation method and applications thereof. The monomer compound provided by the invention has a structure represented by a formula (1), is a temperature-resistant and salt-resistant functional monomer, can improve the tackifying property,the temperature resistance and the salt resistance of a copolymer after being introduced into the copolymer, and can make the copolymer have a certain surface activity so as to be well applied to theoil extraction process of an oil field.
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Paragraph 0085-0087; 0090; 0091; 0115; 0117; 0120; 0121
(2020/04/17)
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- A Photochemical Ligation System Enabling Solid-Phase Chemiluminescence Read-Out
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The peroxyoxalate chemiluminescence (PO-CL) reaction is among the most powerful and versatile techniques for the detection of hydrogen peroxide (H2O2) and has been employed in various biological and chemical applications over the past 50 years. However, its two-component nature (peroxyoxalate and fluorophore) limits its use. This contribution introduces an innovative and versatile photochemical platform technology for the synthesis of inherently fluorescent PO probes by exploiting the nitrile imine-mediated tetrazole-ene cycloaddition (NITEC) reaction. In the presence of hydrogen peroxide, the pioneered “2-in-1” molecule emits either yellow or blue light, depending on tetrazole (Tz) structure. Even in the absence of base, the emitted light remains visible and H2O2 could be detected in the nanomolar range. Critically, the PO-Tz can be readily incorporated into polymeric materials. As a first application of this promising material, a tailor-made PO-Tz is grafted on poly(divinylbenzene) (PDVB) particles to enable solid-phase chemiluminescence on microspheres.
- Delafresnaye, Laura,Schmitt, Christian W.,Barner, Leonie,Barner-Kowollik, Christopher
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p. 12538 - 12544
(2019/07/15)
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- Novel AB-type benzoxazine monomer and preparation method thereof
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The invention belongs to the technical field of high-performance thermosetting resin, and discloses a novel AB-type benzoxazine monomer and a preparation method thereof. The preparation method comprises the following steps: firstly, synthesizing 4-maleimide phenol by using maleic anhydride and p-aminophenol as raw materials; and then synthesizing the AB-type benzoxazine monomer by using the 4-maleimide phenol, 2-furylamine and paraformaldehyde as raw materials. A melting point of the AB-type benzoxazine monomer is 123 DEG C; after the monomer is molten, a Diels-Alder reaction can be performedbetween a maleimide group and a furan group which are contained in the monomer; firstly, main chain benzoxazine is produced, and then benzoxazine ring opening and ring curing occur by further warming;a curing peak temperature is 213.85 DEG C; and such unique mechanism enables the resin to have good thermal performance. After the monomer is cured, a resin material has a residual carbon rate of 57%at a temperature of 800 DEG C, Td5 of 357 DEG C and Td10 of 401 DEG C. The resin material obtained by the AB-type benzoxazine monomer disclosed by the invention has excellent thermal and mechanical properties and excellent machinability, and is low in production cost and suitable for scale production.
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Paragraph 0029; 0030
(2019/06/07)
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- Alizarin red S-TiO2-catalyzed cascade C(sp3)-H to C(sp2)-H bond formation/cyclization reactions toward tetrahydroquinoline derivatives under visible light irradiation
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A very low amount of organic dye (Alizarin red S) sensitized TiO2 and it was successfully used to catalyze cascade C(sp3)-H to C(sp2)-H bond formation/cyclization reactions under visible light irradiation. The modified TiO2 photocatalyst efficiently, for the first time, advanced [4+2] cyclization of N,N-dimethylanilines and maleimides to the corresponding tetrahydroquinolines in air atmosphere. The reaction proceeds through α-amino radicals without additional oxidant at ambient temperature to afford products in good to excellent yields.
- Hosseini-Sarvari, Mona,Koohgard, Mehdi,Firoozi, Somayeh,Mohajeri, Afshan,Tavakolian, Hosein
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p. 6880 - 6888
(2018/05/04)
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- Solvent-free and room temperature visible light-induced C-H activation: CdS as a highly efficient photo-induced reusable nano-catalyst for the C-H functionalization cyclization of: T -amines and C-C double and triple bonds
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Nano-sized CdS was successfully prepared, fully characterized and applied as a highly efficient reusable photocatalyst for the synthesis of pyrrolo[3,4-c]quinolone and pyrrolo[2,1-a]isoquinoline-8-carboxylate derivatives through a condensation reaction of N,N-dimethylanilines or alkyl 2-(3,4-dihydroisoquinolin-2(1H)-yl)acetates with maleimides via a C-H activation approach under benign and eco-friendly conditions at room temperature without using any solvent and oxidant under visible light irradiation. Besides, the prepared photocatalyst has been successfully applied for the condensation reaction of N,N-dimethylanilines with alkyl but-2-ynedioates or phenyl acetylenes for the synthesis of novel 1,2-dihydroquinoline-3,4-dicarboxylate and aryl-1,2-dihydroquinoline derivatives for the first time. Using this method, all favourable products were obtained in good yields and relatively short reaction times under benign conditions with the application of visible light irradiation, a renewable energy source. The catalyst was easily recovered and reused several times without any loss of its activity.
- Firoozi, Somayeh,Hosseini-Sarvari, Mona,Koohgard, Mehdi
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p. 5540 - 5549
(2019/01/03)
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- Maleimide derivative containing xylose triazole structure and preparation method and application thereof
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The invention discloses a maleimide derivative containing a xylose triazole structure and a preparation method and application thereof. The preparation method comprises the following steps: firstly, synthesizing N-p-hydroxyphenyl maleimide and acetyl xylose triazole salicylaldoxime; then, dissolving the N-p-hydroxyphenyl maleimide and the acetyl xylose triazole salicylaldoxime in absolute ethanol,performing 1,3-dipolar cycloaddition reaction, and introducing acetyl xylose triazole and an isoxazole structure; and finally, suspending an intermediate compound in methanol, slowly dropwise addinga methanol solution of sodium methoxide under nitrogen gas protection, performing heating to room temperature to continue reacting, washing ion exchange resin with methanol, reducing pressure of filtrate to remove methanol to obtain a flaxen solid, and performing column chromatography separation to obtain the maleimide derivative containing the xylose triazole structure. The maleimide derivative containing the xylose triazole structure, prepared by the preparation method disclosed by the invention, has a better tumor cell inhibition effect and provides a basis for further application in the medical field.
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Paragraph 0036
(2018/10/11)
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- Containing galactose triazole structure of the maleimide derivative and its preparation method and application (by machine translation)
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The invention discloses a containing galactose triazole structure of the maleimide derivative and its preparation method and application, first synthetic N - hydroxyl phenyl maleimide and acetyl galactose nitrogen [...] aldoxime, then the N - hydroxyl phenyl maleimide and acetyl galactose nitrogen [...] aldoxime dissolved in ethanol, to 1, 3 - dipolar cycloaddition reaction, introduced into the acetyl galactose triazole and isoxazole structure, finally the intermediate compound suspended in methanol, under the protection of nitrogen slowly dropping sodium methoxide methanol solution, heating to room temperature to continue the reaction, washing the ion exchange resin with methanol, the filtrate is pressure reduced to remove the methanol to obtain the yellow solid, column chromatography separation to obtain the containing galactose triazole structure of maleimide derivatives. The invention preparation containing the semi-lactose triazole structure maleimide derivatives, has strong tumor cell suppression effect, for its further medical field is also provided. (by machine translation)
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Paragraph 0026; 0036; 0038
(2018/10/19)
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- Maleimide derivative containing arabinose triazole structure and preparation method and application thereof
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The invention discloses a maleimide derivative containing an arabinose triazole structure and a preparation method and application thereof. The preparation method comprises the following steps: firstly, synthesizing N-p-hydroxyphenyl maleimide and acetyl arabinose triazole salicylaldoxime; then, dissolving the N-p-hydroxyphenyl maleimide and the acetyl arabinose triazole salicylaldoxime in absolute ethanol, performing 1,3-dipolar cycloaddition reaction, and introducing arabinose triazole and an isoxazole structure; and finally, suspending an intermediate compound in methanol, slowly dropwise adding a methanol solution of sodium methoxide under nitrogen gas protection, performing heating to room temperature to continue reacting, washing ion exchange resin with methanol, reducing pressure offiltrate to remove methanol to obtain a flaxen solid, and performing column chromatography separation to obtain the maleimide derivative containing the arabinose triazole structure. The maleimide derivative containing the arabinose triazole structure, prepared by the preparation method disclosed by the invention, has a better tumor cell inhibition effect and provides a basis for further application in the medical field.
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Paragraph 0036-0038
(2018/10/19)
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- Glucose triazole structure-containing maleimide derivative and preparation method and application thereof
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The invention discloses a glucose triazole structure-containing maleimide derivative and a preparation method and the application thereof. The preparation method comprises the following steps: firstly, synthesizing N-p-hydroxyphenylmaleimide and acetylglucostriazole salicylaldoxime, then dissolving the N-p-hydroxyphenylmaleimide and the acetylglucostriazole salicylaldoxime in absolute ethanol, performing a 1, 3-dipolar cycloaddition reaction, introducing acetylglucostriazole and isoxazole structures, finally suspending an intermediate compound in methanol, slowly dropwise adding a methanol solution of sodium methoxide under the protection of nitrogen, heating to a room temperature for continuing reacting, washing ion exchange resin by using methanol, removing the methanol from a filtrate under reduced pressure to obtain a pale yellow solid, and performing column chromatography separation to obtain the glucose triazole structure-containing maleimide derivative. The glucose triazole structure-containing maleimide derivative prepared by the preparation method provided by the invention has a relatively strong tumor cell inhibiting effect, and a basis is provided for further applicationthereof to the field of medicines.
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Paragraph 0026; 0036; 0037
(2018/10/19)
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- Composition, cured product and laminate
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The present invention addresses the problem of providing a composition that has excellent heat resistance and excellent adhesiveness. The present invention also addresses the problem of providing: a cured product which is obtained by curing this composition; and a laminate which contains this cured product. The present invention also addresses the problem of providing a heat-resistant material, a heat-resistant member, an electronic material and an electronic member, each of which contains this composition. The above-mentioned problems are solved by providing a composition that contains: a (meth)allyl group-containing maleimide compound which is characterized by having a structure that has one or more benzene rings and by having one or more groups each having a (meth)allyl group and one or more groups each having a maleimide group; and a hydroxyl group-containing maleimide compound which is characterized by having a structure that has one or more benzene rings and by having one or more groups each having a hydroxyl group and one or more maleimide groups.
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Paragraph 0181; 0182; 0183; 0190; 0191
(2019/04/26)
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- N-substituted maleimide compound based on drug intermediate as well as preparation and antibacterial activity study thereof
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The invention discloses an N-substituted maleimide compound shown as a formula (I), a preparation method of the compound and application of the compound for inhibiting riziocotinia solani or sclerotinia sclerotiorum. The preparation method comprises the following steps: taking anhydride shown as a formula (II) and organic amines as raw materials, dissolving the raw materials in a solvent acetone, magnetically stirring, completely reacting at room temperature, performing rotary evaporation to remove the solvent acetone, adding methylbenzene to serve as a solvent, carrying out an amidation reaction and a closed-loop dehydration reaction under the actions of stabilizers and a dehydrating agent, separating and purifying the reaction solution after the reaction is ended, thereby obtaining the N-substituted maleimide compound shown as the formula (I). The organic amines refer to chlorobenzylamine, ethanol amine, propanolamine, aminophenol or (R)-(+)-1-(4-metoxybenzene) ethylamine; the stabilizers comprise hydroquinone and anhydrous sodium acetate; the dehydrating agent is triethylamine. The N-substituted maleimide compound disclosed by the invention is simple in preparation method and convenient to operate and has excellent effects on rice sheath blight disease and sclerotinia stem rot. The structural formula is as shown in the specification.
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Paragraph 0055-0057
(2017/10/07)
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- Synthesis and Evaluation of Novel Spiro[oxindole-isoxazolidine] Derivatives as Potent Antioxidants
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The antioxidant activity of isatin derivatives can be described with the presence of enolic hydroxyl group at the second position of the ring because of the keto-enol tautomerism between NH and C O groups of indolone moiety. The reducing ability of the tested compounds was evaluated by their interaction with the stable free radical 1,1-diphenyl-2-picrylhydrazyl (DPPH) at various concentrations. Novel spiro[oxindole-isoxazolidine] derivatives (4a, 4b, 4c, 4d, 4e, 4f, 4g, 4h, 4i) have been synthesized by 1,3-dipolar cycloaddition reactions of variously substituted maleimides (1) with isatin ketonitrone (3) and tested for their in vitro antioxidant potency in the DPPH assay. All the synthesized compounds have been identified as potent in vitro antioxidants.
- Kaur, Manpreet,Singh, Baldev,Singh, Baljit,Arjuna, Anania
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p. 1348 - 1354
(2017/03/27)
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- BUILT-IN ANTIMICROBIAL PLASTIC RESINS AND METHODS FOR MAKING THE SAME
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A built-in and process-adaptive formulation of antimicrobial commodity thermoplastic resins with mixed compositions comprising of a polymer, a backbone linker, and a non-labile antifouling and biocompatible coupling agent which is melt-processable and enabled to be manufactured into finished products in the form of solid, monolith, tube, composite, fiber, film, sheet and varnish without the prerequisite of biocides or antimicrobial additives is disclosed. The said formulation is adapted to thermoforming and thermal curing processes including but not limited to melt compounding, spinning, extrusion, molding, compression foaming and drawing. The antimicrobial property is attributed to the persistent formation of a non-stick bacteria-repellent tethered layer in which the antifouling component of the said formulation is heterogeneously phase separated and/or surface migrated to the surface after product forming in order to minimize adsorption and/or colonization of bacteria.
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Paragraph 0062; 0063
(2017/06/09)
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- Potent Nematicidal Activity of Maleimide Derivatives on Meloidogyne incognita
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Different maleimide derivatives were synthesized and assayed for their in vitro activity on the soil inhabiting, plant-parasitic nematode Meloidogyne incognita, also known as root-knot nematode. The compounds maleimide, N-ethylmaleimide, N-isopropylmaleimide, and N-isobutylmaleimide showed the strongest nematicidal activity on the second stage juveniles of the root-knot nematode with EC50/72h values of 2.6 ± 1.3, 5.1 ± 3.4, 16.2 ± 5.4, and 19.0 ± 9.0 mg/L, respectively. We also determined the nematicidal activity of copper sulfate, finding an EC50 value of 48.6 ± 29.8 mg/L. When maleimide at 1 mg/L was tested in combination with copper sulfate at 50 mg/L, we observed 100% mortality of the nematodes. We performed a GC-MS metabolomics analysis after treating nematodes with maleimide at 8 mg/L for 24 h. This analysis revealed altered fatty acids and diglyceride metabolites such as oleic acid, palmitic acid, and 1-monopalmitin. Our results suggest that maleimide may be used as a new interesting building block for developing new nematicides in combination with copper salts.
- Eloh, Kodjo,Demurtas, Monica,Mura, Manuel Giacomo,Deplano, Alessandro,Onnis, Valentina,Sasanelli, Nicola,Maxia, Andrea,Caboni, Pierluigi
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p. 4876 - 4881
(2016/07/06)
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- Synthesis and characterization of schiff base metal complexes and reactivity studies with malemide epoxy resin
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A novel malemide epoxy containing Co(II), Ni(II) and Cu(II) ions have been synthesized by curing malemide epoxy resin (MIEB-13) and Co(II), Ni(II) and Cu(II) complexes of macrocyclic bis-hydrazone Schiff base. The Schiff base was synthesized by reacting 1,4-dicarbnyl phenyl dihydrazide with 2,6-diformyl-4-methyl phenol. The Schiff base and its Co(II), Ni(II) and Cu(II) complexes have been characterized by elemental analyses, spectral (IR, 1H NMR, UV-vis., FAB mass, ESR), thermal and magnetic data. The curing reaction of maleimide epoxy compound with metal complexes was studied as curing agents. The stability of cured samples was studied by thermo-gravimetric analyses and which have excellent chemical (acid/alkali/solvent) and water absorption resistance. Further, the scanning electron microscopy (SEM) and definitional scanning colorimetric (DSC) techniques were confirmed the phase homogeneity of the cured systems.
- Lakshmi,Shivananda,Prakash, Gouda Avaji,Isloor, Arun M,Mahendra
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p. 473 - 482
(2012/05/04)
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- A facile and economical procedure for the synthesis of maleimide derivatives using an acidic ionic liquid as a catalyst
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Seven maleimide derivatives were synthesized in good yields and high purity from the corresponding maleamic acids using a Bronsted acidic room temperature ionic liquid (RTIL) as a catalyst. The products were obtained through merely a decanting and removal of the solvent, suggesting that this procedure is superior to the conventional routes, in which the strong organic/inorganic acids were used as the catalysts, as well as a complicated post-processing procedure for the separation and purification of the products was employed.
- Li, Kai,Yuan, Chao,Zheng, Shijun,Fang, Qiang
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p. 4245 - 4247
(2012/08/28)
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- Synthesis of co(II), Ni(II) and Cu(II) complexes from schiff base ligand and reactivity studies with thermosetting epoxy resin
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A hybrid thermosetting maleimido epoxy compound 4-(N-maleimidophenyl) glycidylether (N-MPGE) containing Co(II), Ni(II) and Cu(II) ions was prepared by curing N-MPGE and tetradentate Schiff base Co(II), Ni(II) and Cu(II) complexes. The curing polymerization reaction of N-MPGE with metal complexes as curing agents was studied. The cured samples were studied for thermal stability, chemical (acid/alkali/solvent) and water absorption resistance and homogeneity of the cured systems. The tetradentate Schiff base, 3-[(Z)-2-piperazin-1-yl- ethylimino]-1,3-dihydro indol-2-one was synthesized by the condensation of Isatin (Indole-2, 3-dione) with 1-(2-aminoethyl)piperazine (AEP). Its complexes with Co(II), Ni(II) and Cu(II) have been synthesized and characterized by microanalysis, conductivity, Uv-Visible, FT-IR, TGA and magnetic susceptibility measurements. The spectral data revealed that the ligand acts as a neutral tetradentate Schiff base and coordinating through the azomethine nitrogen, two piperazine nitrogen atoms and carbonyl oxygen.
- Lakshmi,Shivananda,Prakash, Gouda Avaji,K. Rama, Krishna Reddy,Mahendra
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p. 1613 - 1619
(2011/12/14)
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- Reactivity studies of maleimide epoxy resin with long chained amines
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After phenylmaleimido group was successfully incorporated into bisphenol-A type epoxy resins (B-13 ) to result in compound possessing both oxirane ring and maleimide reactive groups. The cured maleimide epoxy samples are obtained by thermally curing of the maleimide epoxy (MIE) compounds with aliphatic long chained amines such as Tetraethylenepentamine (TEPA), Bishexamethylenetriamine (BHMT), 2-methyl pentamethylenediamine (2-MPMDA) and 2,2,4-trimethy diamines (2,2,4-TMDA) exhibited excellent thermal stability and good chemical (acid/alkali/solvent) and water absorption resistance. Morphological studies by the SEM technique further confirmed the phase homogeneity net work of the cured systems.
- Lakshm,Shivanand,Mahendr
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p. 725 - 728
(2012/03/26)
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- Preparation and reactivity studies of maleimidophenyl glycidylether with amines
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The hybrid thermosetting maleimido epoxy compound 4-(N-maleimidophenyl) glycidylether (N-MPGE) was prepared by reacting N-(4-hydroxyphenyl) maleimide (HPM) with epichlorohydrin by using benzyltrimethylammonium chloride as a catalyst. The resulting compound possessed both the oxirane ring and maleimide group. The curing reaction of N-MPGE with amines as curing agents such as tetraethylenepentamine (TEPA), bishexamethylenetriamine (BHMT), 2-methyl pentamethylenediamine (2-MPMDA) and 2,2,4-trimethy diamines (2,2,4-TMDA) was studied. The cured samples exhibited good thermal stability and excellent chemical (acid/alkali/solvent) and water absorption resistance. Morphological studies by the SEM technique further confirmed the phase homogeneity network of the cured systems.
- Lakshmi,Shivananda,Mahendra
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- Synthesis of new azo compounds based on n-(4-hydroxypheneyl)maleimide and n-(4-methylpheneyl)maleimide
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Maleic anhydride was reacted with p-aminophenol and p-toluidine in the presence of di-phosphorus pentoxide (P2O5) as a catalyst to produce two compounds: N-(4-hydroxyphenyl) maleimide (I) and N-(4-methylphenyl)maleimide (II). The new azo compounds I(a-c) and II(a-c) were prepared by the reaction of I and II with three different aromatic amines, namely aniline, p-aminophenol and p-toluidine. The structures of these compounds were confirmed by CHN, FT-IR, 1H-NMR, 13C-NMR, mass spectrum and UV/Vis spectroscopy.
- Mohammed, Issam Ahmed,Mohammed, Asniza
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experimental part
p. 7498 - 7508
(2011/02/22)
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- Synthesis, characterization and curing studies of thermosetting epoxy resin with amines
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A new hybrid thermosetting maleimido epoxy compound 4-(N-maleimidophenyl) glycidylether (N-MPGE) is prepared by reacting N-(4-hydroxyphenyl) maleimide (HPM) with Epichlorohydrin by using benzyltrimethylammonium chloride as a catalyst. The resulting compound possesses both the oxirane ring and maleimide group. The curing reaction of these maleimidophenyl glycidylether epoxy compound (N-MPGE) with amines as curing agents such as ethylendiamine (EDA), diethylentriamine (DETA) and triethylenetetramine (TETA), aminoethylpiperazine (AEP) and isophoronediamine, IPDA), are studied. Incorporation of maleimide groups in the epichlorohydrin provides cyclic imide structure and high cross-linking density to the cured resins. The cured samples exhibited good thermal stability, excellent chemical (acid/alkali/solvent) and water absorption resistance. Morphological studies by the SEM technique further confirmed the phase homogeneity net work of the cured systems.
- Lakshmi,Shivananda,Mahendra
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scheme or table
p. 2272 - 2278
(2010/11/05)
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- Development of polymeric phase change materials on the basis of diels-alder chemistry
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Diels-Alder (DA) chemistry is increasing popular due to its simplicity and efficiency; however, one concept that has yet to be thoroughly explored is incorporation of DA linkages within materials for the development of polymeric phase change materials. It is well established that the retro-DA reaction results in a large endotherm, which could be a potential energy sink for phase change materials. Hydroxyl-terminated polybutadiene (HTPB) was selected as a prepolymer and modified with different DA linkages. Cured materials were prepared upon addition of diisocyanates and their physical properties of the cured elastomers were investigated using thermogravimetric analysis (TGA), differential scanning calorimetry (DSC) and rheological testing. The resulting thermally responsive HTPB (TR-HTPB) exhibited the ability to absorb energy and flow at elevated temperatures. Furthermore, they displayed unusual responses to repeated thermal cycling, including changes in thermal absorption and rheological characteristics.
- Swanson, John P.,Rozvadovsky, Svetlana,Seppala, Jonathan E.,MacKay, Michael E.,Jensen, Robert E.,Costanzo, Philip J.
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scheme or table
p. 6135 - 6141
(2011/11/12)
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- Access to indoles via Diels-Alder reactions of 2-vinylpyrroles with maleimides
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(Chemical Equation Presented) Variously substituted 2-vinylpyrroles underwent an endo-addition [4+2] cycloaddition reaction with maleimides followed by a spontaneous highly diastereoselective (93-98% de) isomerization to give tetrahydroindoles in moderate to excellent yield. Treatment with activated MnO2 in refluxing toluene provided the corresponding indoles in moderate to good yield. This highly convergent methodology for formation of indoles is versatile and the starting materials are conveniently prepared.
- Noland, Wayland E.,Lanzatella, Nicholas P.,Venkatraman, Lakshmanan,Anderson, Nicholas F.,Gullickson, Glen C.
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experimental part
p. 1154 - 1176
(2010/03/04)
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- Synthesis and in vitro evaluation of N-substituted maleimide derivatives as selective monoglyceride lipase inhibitors
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The endocannabinoid 2-arachidonoylglycerol (2-AG) plays a major role in many physiological processes, and its action is quickly terminated via enzymatic hydrolysis catalyzed by monoglyceride lipase (MGL). Regulating its endogenous level could offer therapeutic opportunities; however, few selective MGL inhibitors have been described so far. Here, we describe the synthesis of N-substituted maleimides and their pharmacological evaluation on the recombinant human fatty acid amide hydrolase (FAAH) and on the purified human MGL. A few N-arylmaleimides were previously described (Saario, S. M.; Salo, O. M.; Nevalainen, T.; Poso, A.; Laitinen, J. T.; Jarvinen, T.; Niemi, R. Characterization of the Sulfhydryl-Sensitive Site in the Enzyme Responsible for Hydrolysis of 2-Arachidonoylglycerol in Rat Cerebellar Membranes. Chem. Biol. 2005, 12, 649-656) as MGL inhibitors, and along these lines, we present a new set of maleimide derivatives that showed low micromolar IC50 and high selectivity toward MGL vs FAAH. Then, structure-activity relationships have been investigated and, for instance, 1-biphenyl-4-ylmethylmaleimide inhibits MGL with an IC50 value of 790 nM. Furthermore, rapid dilution experiments reveal that these compounds act as irreversible inhibitors. In conclusion, N-substituted maleimides constitute a promising class of potent and selective MGL inhibitors.
- Matuszak, Nicolas,Muccioli, Giulio G.,Labar, Geoffray,Lambert, Didier M.
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experimental part
p. 7410 - 7420
(2010/04/30)
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- Design and synthesis of a novel DNA-encoded chemical library using Diels-Alder cycloadditions
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DNA-encoded chemical libraries are increasingly being employed for the identification of binding molecules to protein targets of pharmaceutical relevance. Here, we describe the synthesis and characterization of a DNA-encoded chemical library, consisting of 4000 compounds generated by Diels-Alder cycloaddition reactions. The compounds were encoded with unique DNA fragments which were generated through a stepwise assembly process and serve as amplifiable bar codes for the identification and relative quantification of library members.
- Buller, Fabian,Mannocci, Luca,Zhang, Yixin,Dumelin, Christoph E.,Scheuermann, Joerg,Neri, Dario
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supporting information; experimental part
p. 5926 - 5931
(2009/05/31)
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- Composition for forming organic insulating film and organic insulating film formed from the same
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Disclosed herein is a composition for forming an organic insulating film and an organic insulating film formed from the composition. An exemplary composition comprises an insulating polymer having a maleimide structure, a crosslinking agent and a photoacid generator so as to form a crosslinked structure. The organic insulating film has excellent chemical resistance to organic solvents used in a subsequent photolithographic process and can improve the electrical properties of transistors.
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Page/Page column 11-12
(2010/11/28)
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- Thermally cleavable surfactants
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Two new surfactant molecules are reported which contain thermally labile Diels-Alder adducts connecting the polar and non-polar sections of each molecule. The two surfactants possess identical non-polar dodecyl tail segments but exhibit different polar headgroups. The surfactants become soluble in water when anionic salts are formed through the deprotonation of the surfactant headgroups by the addition of potassium hydroxide. When either surfactant is exposed to temperature above about 60° C., the retro Diels-Alder reaction occurs, yielding hydrophilic and hydrophobic fragments and the aqueous solutions of the surfactants subsequently exhibit loss of all surface-active behavior.
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Page/Page column 6-7
(2008/06/13)
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- Surface-induced alignment of pentacene by photo-alignment technology for organic thin film transistors
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A series of highly soluble maleimide-based polymers with photoreactive pendant group were synthesized and used as a gate dielectric insulator for organic thin film transistors. Photoalignment properties were characterized by UV-visible spectroscopy and the alignment of liquid crystals. Photopolymerization of polymer-coated organic thin film transistors with linearly polarized UV light induces anisotropy in field-effect mobility. The gate dielectric insulator based on the photoalignable maleimide shows higher field-effect mobility and on/off current ratio than those from a SiO2 gate dielectric insulator with the values of 0.3 cm2 V-1 s-1 and 104, respectively. Our results demonstrate that the photo-induced anisotropy of alignment films to control the molecular order of semiconducting pentacene is a promising technology for improving the performance of organic thin film transistors. The Royal Society of Chemistry 2005.
- Jin, Sung-Ho,Seo, Hwang-Un,Nam, Dong-Hee,Shin, Won Suk,Choi, Jung-Hei,Yoon, Ung Chan,Lee, Jae-Wook,Song, Jung-Gun,Shin, Dong-Myung,Gal, Yeong-Soon
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p. 5029 - 5036
(2007/10/03)
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- NEW EFFECTOR CONJUGATES, PROCESS FOR THEIR PRODUCTION AND THEIR PHARMACEUTICAL USE
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Conjugates of epothilones and epothilone derivatives (as effectors) with suitable biomolecules (as recognition units) are described. Their production is carried out by the effectors being reacted with suitable linkers, and the compounds that are produced are conjugated to the recognition units. The pharmaceutical use of the conjugates for treating proliferative or angiogenesis-associated processes is described.
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Page/Page column 47
(2010/02/06)
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- Reversible and irreversible inhibitory activity of succinic and maleic acid derivatives on acetylcholinesterase
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Aryl succinic and maleic acid derivatives are potent inhibitors of bovine acetylcholinesterase in vitro. Succinic acid aminophenol derivatives 1b-e and 2b-d act as reversible inhibitors of acetylcholinesterase, while maleic acid aminophenol derivatives 3b-d and 4c-e act as choline subsite-directed irreversible inhibitors, detected by dialysis in the presence of edrophonium. Linear relationships between the logarithm of the velocity of hydrolysis of acetylcholine plotted against the time of incubation at several different inhibitor concentrations were determined. The Ki for reversible competitive inhibitors was determined. For irreversible inhibitors the Ki for the dissociation constant of the enzyme-inhibitor complex at the beginning of the recognition process was also determined as well as the inactivation constant of the enzyme-inhibitor adduct formation k+2 and the bimolecular inhibition constant ki for the inhibition of acetylcholinesterase by aminophenol derivatives 3b-d and 4c-e. The conclusions of this study can be summarized as follows for both families: (a) the aromatic moiety played a critical role in the recognition of the active site; (b) in case of the reversible inhibitor, when the ester function took the place of the hydroxyl fragment, there was an important increase in the affinity; and (c) the distance between phenolic hydroxyl and nitrogen was critical because the inhibition is ortho?metapara.
- Trujillo-Ferrara,Vazquez, Ivan,Espinosa, Judith,Santillan, Rosa,Farfan, Norberto,Hoepfl, Herbert
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p. 313 - 322
(2007/10/03)
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- Synthesis and antimicrobial activities of N-substituted imides
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In the field of our research programs concerning novel antimicrobial agents, a series of N-substituted imides was synthesized. These compounds were obtained by cyclization of amido-acids in acetic anhydride/sodium acetate or hexamethyldisilazane/zinc bromide for the hydroxy-aromatic derivatives. The hydroxy-alkyl maleimides were directly prepared by condensation of the corresponding amino-alcohol with maleic anhydride in boiling toluene. Most of N-substituted maleimides showed an interesting antimicrobial activity towards bacteria from the ATCC collection (Staphylococcus aureus ATCC 25923, Enterococcus faecalis ATCC 29212, Escherichia coli ATCC 25922 and Pseudomonas aeruginosa ATCC 27853) but the MIC values for P. aeruginosa were always high (128 μg/ml). The imides with alkyl substituents showed higher activities than aromatic analogues with MIC values in the range of 8-32 μg/ml. Comparatively, succinimides were practically inactive.
- Zentz, Frederic,Valla, Alain,Le Guillou, Regis,Labia, Roger,Mathot, Anne-Gabrielle,Sirot, Danielle
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p. 421 - 426
(2007/10/03)
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- Preparation of N-substituted maleimides by use of tin catalysts
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A process for the preparation of N-substituted maleimides by conducting heat-dehydration and dehydrating imidization of N-substituted maleamic acids under azeotropic distillation of generated water in a solvent mixture containing a solvent capable of forming water azeotrope and an organic aproptic polar solvent, in the presence as catalyst of metallic tin, tin oxide, a tin salt of a maleamic acid or a tin compound which forms a thin salt of the N-substituted maleamic acid in the reaction system.
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- Monofunctional crosslinking imidophenols
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Resins are prepared from polysulfone and polyethersulfone polymers that bear functional groups derived from compounds that are condensation products of amino-phenols and acid anhydrides. The polymers are prepared by coreacting aromatic compounds holding two hydroxyl groups, aromatic compounds holding two active halogen groups, and the condensation product of amino-phenol and acid anhydride, the condensation product holding one hydroxyl group. The resulting product has a molecular weight between about 1,000 and 40,000, preferably between about 5,000 and 30,000, and can be cross-linked to form a resin that is thermoplastic and solvent resistant.
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- Process for the production of N-(hydroxyphenyl) maleimides
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N-(hydroxyphenyl) maleimides of the general formula STR1 where R' stands for H, CH3, C2 H5, F, Cl, Br or I and n is an integer of 1-5 are produced by treating the corresponding maleamic acid or by treating the ester of said N-(hydroxyphenyl) maleimide at a temperature of 0-150° C. in the presence of at least one dehydrating agent selected from the group consisting of oxides and oxyacids of sulfur or phosphorus and alkali metal and alkaline earth metal salts of the said oxyacids. The corresponding maleamic acid can be obtained by reacting an aminophenol having one or more hydroxyl groups on its phenyl nucleus with maleic anhydride. The esters of the N-(hydroxyphenyl maleimide) can be obtained by reacting said aminophenol and said maleic anhydride in the presence of a conventional acid anhydride dehydrating agent and a conventional imide-forming cyclization catalyst.
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