- Solvent free preparation of n-substituted maleanilic acid
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Six N-maleanilic acids namely N-(4-carboxy)maleanilic acid (CAMAA), N-(4- bromo)maleanilic acid (BMAA), N-(4-hydroxy)maleanilic acid (HMAA), N-(3-hydroxy)maleanilic acid (mHMAA), N-(4-chloro)maleanilic acid (CMAA) and N-(4-methyl)maleanilic acid (MMAA) we
- Saedi, Habib
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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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- 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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supporting information
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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supporting information
p. 5540 - 5549
(2019/01/03)
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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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- 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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experimental part
p. 4245 - 4247
(2012/08/28)
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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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scheme or table
p. 473 - 482
(2012/05/04)
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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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experimental part
p. 725 - 728
(2012/03/26)
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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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scheme or table
p. 1613 - 1619
(2011/12/14)
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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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scheme or table
p. 73 - 82
(2012/05/07)
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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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- 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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- Synthesis and antifungal activity of N-(alkyl/aryl)-2-(3-oxo-1,4- benzothiazin-2-yl)acetamide
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A series of N-(alkyl/aryl)-2-(3-oxo-1,4-benzothiazin-2-yl)acetamide have been synthesized by condensation of substituted amines with maleic anhydride (MA) followed by cyclization with o-aminothiophenol (o-ATP). All the compounds have been screened for their antifungal activity against Tricophyton rubrum, Epidermophyton floccosum and Malassazia furfur. In the primary screening, some of the compounds exhibited appreciable activity. The structures of the synthesized compounds 7a-z have been established on the basis of elemental analysis and spectral data.
- Gupta,Wagh
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p. 697 - 702
(2007/10/03)
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- Solvent-free synthesis of arylamides and arylimides, analogues of acetylcholine
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Several arylamides and arylimides, novel inhibitors of acetylcholinesterase, were obtained under solventless conditions; the target molecules were produced with a good overall yield and short reaction times. 2017-2023 Copyright Taylor & Francis, Inc.
- Trujillo-Ferrara,Correa-Basurto, Jose,Espinosa, Judith,Garcia, Jazmin,Martinez, Francisco,Miranda, Rene
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p. 2017 - 2023
(2007/10/03)
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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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- 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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- 1H and 13C NMR spectra for a series of arylmaleamic acids, arylmaleimides, arylsuccinamic acids and arylsuccinimides
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The 1H and 13C NMR spectra of 17 succinic anhydride derivatives and 25 maleic anhydride derivatives were completely assigned using one- and two-dimensional NMR techniques. Copyright
- Trujillo-Ferrara, Jose,Santillan, Rosa,Beltran, Hiram I.,Farfan, Norberto,Hoepfl, Herbert
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p. 682 - 686
(2007/10/03)
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- Preparation of N-aryl-substituted spiro-β-lactams via staudinger cycloaddition
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The interest in the study of β-lactams continues due to their therapeutic importance as antibiotics. In this work, six spiro-β-lactams (7a-7c, 8a-8c) have been prepared using the [2+2] cycloaddition of isomaleimides to acid chlorides. The heterobicyclic structures obtained have been characterized by mass spectrometry, IR, NMR spectroscopy, and for compounds 7a, 7b, and 8b the X-ray crystallographic study showed a nearly planar arrangement for the β-lactam ring.
- Barba, Victor,Hernandez, Cecilia,Rojas-Lima, Susana,Farfan, Norberto,Santillan, Rosa
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p. 2025 - 2032
(2007/10/03)
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- INFLUENCE OF MEDIUM AND SUBSTITUENTS ON ACYLATION OF AROMATIC AMINES AND THEIR POLYMERIC ANALOGS WITH MALEIC ANHYDRIDE
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Correlation relationships describing the influence of substituents and solvents on the rate of acylation of aromatic amines and their polymeric analogs with maleic anhydride have been derived.
- Donya, A. P.,Pakter, M. K.,Sokhina, S. I.
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p. 2093 - 2097
(2007/10/02)
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- Preparation process of N-substituted maleimides
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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 aprotic polar solvent, in the presence as catalyst of a zinc salt of a maleamic acid, metallic zinc or a zinc compound which forms a zinc salt of the N-substituted maleamic acid in the reaction system.
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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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- Spectrophotometric and Titrimetric Determination of Carboxylic Acid Anhydrides
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Two redox methods are described for the determination of carboxylic acid anhydrides involving reaction with either an excess of 4-aminophenol or a measured but excessive amount of sulfanilamide and photometric titration of N-acyl-4-aminophenol with 2-iodylbenzoate by measuring the absorbance of orange-red product at 444 nm or the residual amount of sulfanilamide is determined by titration with chloramine-T in the presence of acidified potassium bromide using methyl red as visual indicator.Mixtures of certain anhydrides have also been analyzed by the 2-iodylbenzoate method.The methods are rapid, precise, and accurate.No correlation is needed if carboxylic and mineral acids are also present.Carboxylic acid chlorides also react quantitatively.
- Verma, Krishna K.,Tyagi, Pramila
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p. 2157 - 2160
(2007/10/02)
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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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