- Maleimide fused boron-fluorine complexes: Synthesis, photophysical and electrochemical properties
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Novel boron fluorine complex molecules were designed and synthesized using the maleimide core moiety. Significant features such as a large Stoke shift, high quantum yield, and long range absorption and emission wavelengths were observed for these molecules. The lower LUMO level of these molecules indicates their potential application as electron transport materials. The optical band gap was calculated and compared by using UV-absorption edge, density functional theory and electrochemical studies, revealing the charge transfer characteristics.
- Thale, Pranila B.,Borase, Pravin N.,Shankarling, Ganapati S.
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- Approach to the Synthesis of Unsymmetrical/Symmetrical Maleimides via Desulfitative Arylation at Different Temperatures
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New routes toward selective synthesis of both mono-and diaryl maleimides have been innovated. The mere requirement to this end is through the increase of temperature. The method works effectively for maleic anhydride and maleic acid as well. Also, the fir
- Abbasnia, Masoumeh,Sheykhan, Mehdi,Ghaffari, Tahereh,Safari, Elham
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p. 11688 - 11698
(2020/10/23)
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- Structures and photophysical properties of 3,4-diaryl-1H-pyrrol-2,5-diimines and 2,3-diarylmaleimides
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Structural features of 3,4-diaryl-1H-pyrrol-2,5-diimines and their derivatives have been studied by molecular spectroscopy techniques, single-crystal X-ray diffraction, and DFT calculations. According to the theoretical calculations, the diimino tautomeri
- Afanasenko, Anastasiia M.,Boyarskaya, Dina V.,Boyarskaya, Irina A.,Chulkova, Tatiana G.,Grigoriev, Yakov M.,Kolesnikov, Ilya E.,Avdontceva, Margarita S.,Panikorovskii, Taras L.,Panin, Andrej I.,Vereshchagin, Anatoly N.,Elinson, Michail N.
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p. 554 - 561
(2017/06/20)
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- Diarylmaleic anhydrides: unusual organic luminescence, multi-stimuli response and photochromism
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Diarylmaleic anhydride derivatives containing benzene (BPMA), thiophene (BTMA) and indole (BIMA) exhibit diverse and distinct fluorescence: aggregation-caused quenching (ACQ) of red emission of BIMA, blue aggregation-induced emission (AIE) of BPMA, and green dual-state emission (DSE) of BTMA in both solution and the solid state. Theoretical calculation and crystal structure analysis indicate that intramolecular and intermolecular interactions are responsible for their different emission behavior. A series of DSE-active molecules with full-color emission could be developed for the first time, through modification of the structures of BPMA and BIMA. Interestingly, BTMA and BPMA display multi-stimuli-responsive luminescence with a high-contrast (Δλem > 100 nm) and an unusual photochromic phenomenon in dichloromethane, which were utilized to construct rewritable data storage and mimic molecular logic operation (4-to-2 encoder and 1?:?2 demultiplexer), respectively.
- Mei, Xiaofei,Wang, Jingwei,Zhou, Zhonggao,Wu, Shiyi,Huang, Limei,Lin, Zhenghuan,Ling, Qidan
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supporting information
p. 2135 - 2141
(2017/03/09)
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- Direct cycle between co-product and reactant: An approach to improve the atom economy and its application in the synthesis and protection of primary amines
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Two important goals of green chemistry are to maximize the efficiency of reactants and to minimize the production of waste. In this study, a novel approach to improve the atom economy of a chemical process was developed by incorporating a direct cycle between a co-product and a reactant of the same reaction. To demonstrate this concept, recoverable 3,4-diphenylmaleic anhydride (1) was designed and used for the atom-economical synthesis of aliphatic primary amines from aqueous ammonia. In each individual cycle, only ammonia and alkyl halide were consumed, and 1 was recovered in nearly a quantitative yield. In this approach for developing atom-economical protecting agents, 1 showed good performance as a recoverable protecting agent for primary amines. The broad substrate scope, good tolerance to various reaction conditions, and high reaction and recovery rates make 1 a valuable complement to conventional primary amine protecting agents.
- Guan, Qi,Jiang, Mingyang,Wu, Junhui,Zhai, Yanpeng,Wu, Yue,Bao, Kai,Zhang, Weige
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p. 5794 - 5799
(2016/11/06)
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- A method for the production of primary amines
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The invention relates to the field of chemical industry and particularly relates to a method for preparing primary amine by using the raw materials including halogenated hydrocarbon (or hydrocarbon alcohol sulfonate) and ammonia water (or formamide). The method comprises the following three steps: (1) imidization: 3,4-diarylfuran-2,5-diketone (I) reacts with ammonia (or formamide) and the like to obtain 3,4-diaryl-1H-pyrrole-2,5-diketone (II); (2) N-hydrocarbylation: 3,4-diaryl-1H-pyrrole-2,5-diketone (II) generates an N-hydrocarbylation reaction with halogenated hydrocarbon (or hydrocarbon alcohol sulfonate) in the presence of alkali to obtain N-hydrocarbyl-3,4-diaryl-1H-pyrrole-2,5-diketone (III); and (3) hydrolysis: N-hydrocarbyl-3,4-diaryl-1H-pyrrole-2,5-diketone (III) is subjected to alkali hydrolysis to obtain primary amine and the generated 2,3-diaryl maleate is subjected to acid treatment and automatic ring closing to form 3,4-diaryl furan-2,5-diketone (I) which is subjected to imidization and directly applied to the N-hydrocarbylation reaction. The method provided by the invention has the characteristics that the 3,4-diaryl furan-2,5-diketone can be circularly used at a high recovery rate, the molar ratio of the raw materials is low, and the yield of the product primary amine is high.
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Paragraph 0087; 0088
(2016/10/09)
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- Assembly of Polysubstituted Maleimides via Palladium-Catalyzed Cyclization Reaction of Alkynes with Isocyanides
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An efficient and convenient palladium-catalyzed cyclization reaction of alkynes with isocyanides is described herein. This protocol allows the practical synthesis of many valuable polysubstituted maleimide derivatives after hydrolysis with a broad scope of substrates and mild reaction conditions. C-C, CO, and C-N bonds were constructed in this transformation with isocyanide serving as both C and N sources.
- Hu, Weigao,Zheng, Jia,Li, Jianxiao,Liu, Bifu,Wu, Wanqing,Liu, Haiyang,Jiang, Huanfeng
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p. 12451 - 12458
(2016/12/23)
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- Diarylmaleimide fluorophores: Intensely emissive low-band-gap guest for single white polymers with highly efficient electroluminescence
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A series of novel single white polymers, PFPMs and PFTMs, were designed and synthesized by introducing a green diphenylmaleimide (PM, λem = 500 nm) or yellow dithienylmaleimide (TM, λem = 557 nm) fluorophore guest into a blue polyfluorene (PF) host. By adjusting the feed ratio of the maleimide unit and fluorene unit, the resulting single white polymers exhibited a dual emission, including blue emission (415/439 nm) from PF and yellow (546 nm) or red (659 nm) emission from the PM or TM guest. The large red-shift in emission of the PM and TM in the backbone of the polymers originates from their conjugated structure being extended by the fluorene units. All the polymers show similar and high thermal stability and large solubility in common organic solvents. Their electroluminescent properties were investigated in single-emitting-layer devices fabricated by a solution process with the configuration of ITO/PEDOT:PSS/polymer/TPBI/LiF/Al. PFPM03, containing 0.3% PM, exhibited an excellent white electroluminescent performance for the effective and incomplete energy transfer from the PF host to the maleimide guest. The white device based on annealed PFPM03 at 140 °C for 30 min could be further improved to reach a maximal current efficiency of 8.14 cd A-1, power efficiency of 3.93 lm W-1, and external quantum efficiency of 3.78% with CIE coordinates of (0.34, 0.41).
- Wei, Kexi,Wen, Guixiu,Zhao, Yan,Lin, Zhenghuan,Mei, Xiaofei,Huang, Limei,Ling, Qidan
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p. 9804 - 9812
(2016/11/02)
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- New heterocycles of 2,3-diaryl-substituted maleic hydrazides
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2,3-Diaryl-substituted maleic anhydrides were prepared by a modified one-pot synthesis of Perkin condensation using mixed sodium salts of arylglyoxylic acid and arylacetic acid with acetic anhydride in 1,4-dioxane. The treatment of these anhydrides with ammonium bicarbonate, or methanolic hydrazine, offered the corresponding 2,3-diaryl-substituted maleimides and maleic hydrazides (4,5-diaryl-substituted 1,2-dihydropyridazine-3,6-dione), respectively. Evidence obtained from NMR, UV, and mass spectra suggest that 2,3-diaryl-substituted maleic hydrazides do not exhibit monolactim forms. Ring contraction of the diaryl-substituted maleic hydrazide by nitrosation led to the formation of the corresponding maleimide. Interconversion between the corresponding maleic hydrazide and maleimide was observed following equilibrium reaction. Our experiment proposes that the chemistry of 2,3-diaryl-substituted maleic hydrazides rarely involves the function of ethylene moiety and resembles that of succinic hydrazine. Copyright
- Shih, Hsiencheng,Shih, Renshuay J.,Carson, Dennis A.
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experimental part
p. 1243 - 1250
(2012/01/04)
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- Synthesis and PGE2 production inhibition of 1H-furan-2,5-dione and 1H-pyrrole-2,5-dione derivatives
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3,4-Diphenyl-substituted 1H-furan-2,5-dione and 1H-pyrrole-2,5-dione derivatives were synthesized and evaluated for the inhibitory activities on LPS-induced PGE2 production in RAW 264.7 macrophage cells. Both 1H-furan-2,5-dione and 1H-pyrrole-2,5-dione rings as main scaffolds were easily obtained using one of three synthetic methods. Among the compounds investigated, 1H-3-(4-sulfamoylphenyl)-4-phenyl-pyrrole-2,5-dione (6l) showed a strong inhibitory activity (IC50 = 0.61 μM) of PGE2 production.
- Moon, Jong Taik,Jeon, Ji Young,Park, Hang Ah,Noh, Young-Soo,Lee, Kyung-Tae,Kim, Jungahn,Choo, Dong Joon,Lee, Jae Yeol
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scheme or table
p. 734 - 737
(2010/06/22)
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- CYCLOOXYGENASE-2 INHIBITORS
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The present invention relates to lH-pyrrole or furan-2,5dione derivatives and a pharmaceutical composition for inhibiting cyclooxygenase-2(COX-2), more specifically for treating or preventing inflammation, an allergic disorder, inflammatory dermatosis, an immunologic disorder, a neurodegenerative disorder, arthritis, pain or fever comprising the same.
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Page/Page column 12
(2009/01/20)
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- Design, synthesis, and biological evaluation of 3,4-diarylmaleimides as angiogenesis inhibitors
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The new analogue 2 of combretastatin A-4 was discovered to be an inhibitor of tubulin polymerization with an IC50 of 7.6 μM and reduced angiogenesis in the in vivo chick embryo model. Interestingly, in a series of 2,3-diarylmaleimides closely r
- Peifer, Christian,Stoiber, Thomas,Unger, Eberhard,Totzke, Frank,Sch?chtele, Christoph,Marmé, Dieter,Brenk, Ruth,Klebe, Gerhard,Schollmeyer, Dieter,Dannhardt, Gerd
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p. 1271 - 1281
(2007/10/03)
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- Derivative of α,β-dicyanostilbene: Convenient precursor for the synthesis of diphenylmaleimide compounds, E-Z isomerization, crystal structure, and solid-state fluorescence
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A convenient and efficient procedure was developed for preparing 3,4-diaryl-substituted maleimides through the improved synthesized diaryl-substituted fumaronitrile. The synthesis of diphenyl-substituted fumaronitrile derivatives from phenylacetonitrile compounds was analyzed and improved. We found the stoichiometry of the sodium methoxide and the concentration of the starting material, phenylacetonitrile derivatives, were crucial for the high yield and easy purification of the products. Particularly, bis(4-bromophenyl)fumaronitrile, bis(3-trifluoromethylphenyl)fumaronitrile, and bis(4-methoxyphenyl)fumaronitrile were isolated in good yields of 70-90% by simple suction filtration. In addition, 1H NMR provided compelling evidence that the E-Z isomerization was involved in the formation reaction of the maleimide compounds from either fumaronitrile or maleonitrile derivatives. Single-crystal X-ray structures of these three fumaronitrile derivatives, the first three of the kind, were obtained, revealing the nonplanar molecular structure. We ascribe the strong solid-state fluorescence of these diphenylfumaronitrile derivatives to the nonplanar structure that inhibits the close packing of the molecule aggregation and thus the fluorescence quenching.
- Yeh, Hsiu-Chih,Wu, Wei-Ching,Wen, Yuh-Sheng,Dai, De-Chang,Wang, Juen-Kai,Chen, Chin-Ti
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p. 6455 - 6462
(2007/10/03)
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- The colourful fluorescence from readily-synthesised 3,4-diaryl-substituted maleimide fluorophores
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A new synthesis procedure has been developed for a series of maleimide-based fluorophores, exhibiting a large variation of emission spectra spanning the entire visible range.
- Yeh, Hsiu-Chih,Wu, Wei-Ching,Chen, Chin-Ti
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p. 404 - 405
(2007/10/03)
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- Electronic effects in the acid-promoted deprotection of N-2,4-dimethoxybenzyl maleimides
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Cleavage of several 2,4-dimethoxybenzylmaleimides could be performed employing TFA in anisole. Electronic effects exemplified by varying the substitution present on the maleimide resulted in a variation in the rate of the deprotection. In contrast, 2,4-dimethoxybenzylsuccinimides were inert to the conditions.
- Watson, Daniel J.,Dowdy, Eric D.,Li, Wen-Sen,Wang, Jianji,Polniaszek, Richard
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p. 1827 - 1830
(2007/10/03)
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- A new one step synthesis of maleimides by condensation of glyoxylate esters with acetamides
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Bisphenyl, bisheteroaryl, indolylaryl and indolylcycloalkyl maleimides are prepared in one step and 67-99% yield by condensation of glyoxylate esters with acetamides using a 1.0 M solution of potassium tert-butoxide in THF. The mechanism of the reaction is discussed.
- Faul, Margaret M.,Winneroski, Leonard L.,Krumrich, Christine A.
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p. 1109 - 1112
(2007/10/03)
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- A mild conversion of maleic anhydrides into maleimides
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Maleic anhydrides are converted into maleimides, at room temperature and in excellent yield, by treatment with a mixture of methanol and hexamethyldisilazane. Esters and nitriles are unaffected under these conditions.
- Davis,Bit
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p. 5201 - 5204
(2007/10/02)
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- The Chemistry of 3-(α-Cyanobenzylidene)-1-phenyltriazenes and Their Conversion to Diarylmaleimides and Phenanthrene-9,10-dicarboximides
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3-(α-Cyanobenzylidene)-1-phenyltriazine (3a), the product of thermolysis of 5-azido-1,4-diphenyl-1,2,3-triazole (2), is attacked by nucleophilic reagents at the azomethine carbon.Alcohols and phenol give rise to acetals of the N-phenylamidine of phenylgly
- Smith, Peter A. S.,Friar, James Jeffrey,Resemann, Wolfgang,Watson, Andrew C.
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p. 3351 - 3362
(2007/10/02)
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- SYNTHESIS AND PHOTOCHEMICAL REACTIVITY OF O-ALKYLMALEIMIDE
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Irradiation of O-alkylmaleimide, prepared by the reaction of silver maleimide with alkyl bromide, resulted in Norrish type II elimination presumably initiated by γ-hydrogen abstraction of excited carbon-nitrogen double bond.
- Izawa, Yasuji,Yokoi, Kanemasa,Tomioka, Hideo
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p. 1473 - 1476
(2007/10/02)
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