4808-48-4Relevant academic research and scientific papers
Facile Synthesis of γ-Butenolides and Maleic Anhydrides via Annulation of α-Keto Acids and Triazenyl Alkynes
Bao, Xiaodong,Cui, Sunliang,Jin, Jian,Zeng, Linwei
, (2022/02/14)
A facile synthesis of γ-butenolides and maleic anhydrides via annulation of α-keto acids and triazenyl alkynes is described. In this process, α-keto acids and triazenyl alkynes could undergo a self-catalyzed annulation at room temperature to deliver γ-butenolides efficiently, while the further addition of BF3-Et2O furnished maleic anhydrides. Overall, these processes have mild reaction conditions, broad scope, and high efficiency.
Choline hydroxide promoted sustainable one-pot three-component synthesis of 1H-pyrazolo[1,2-a]pyridazine-2-carbonitriles under solvent-free conditions
Vajekar, Shailesh N.,Shankarling, Ganapati S.
supporting information, p. 1147 - 1158 (2020/03/30)
A sustainable one-pot three-component synthesis of novel 1H-pyrazolo[1,2-a]pyridazine-2-carbonitrile derivatives employing a highly efficient, biodegradable, and recyclable choline hydroxide catalyst under solvent-free conditions is demonstrated. The salient features of this protocol are simple workup, mild reaction conditions, short reaction time (10 min), excellent yields (up to 97%), high atom economy, column chromatography-free protocol, and eco-friendliness. Interestingly, the choline hydroxide was recycled up to five cycles without any considerable loss of efficiency. The structures of the products were deduced by their 1H NMR, 13C NMR, and HRLC-MS spectra.
Diarylmaleic anhydrides: unusual organic luminescence, multi-stimuli response and photochromism
Mei, Xiaofei,Wang, Jingwei,Zhou, Zhonggao,Wu, Shiyi,Huang, Limei,Lin, Zhenghuan,Ling, Qidan
, p. 2135 - 2141 (2017/03/09)
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.
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
Guan, Qi,Jiang, Mingyang,Wu, Junhui,Zhai, Yanpeng,Wu, Yue,Bao, Kai,Zhang, Weige
supporting information, p. 5794 - 5799 (2016/11/06)
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.
Maleimide fused boron-fluorine complexes: Synthesis, photophysical and electrochemical properties
Thale, Pranila B.,Borase, Pravin N.,Shankarling, Ganapati S.
supporting information, p. 13947 - 13954 (2015/08/18)
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.
Strong CIE activity, multi-stimuli-responsive fluorescence and data storage application of new diphenyl maleimide derivatives
Zheng, Rong,Mei, Xiaofei,Lin, Zhenghuan,Zhao, Yan,Yao, Huimei,Lv, Wei,Ling, Qidan
, p. 10242 - 10248 (2015/10/12)
A series of benzamide-based diphenyl maleimide derivatives 2a-d with strong crystallization-induced emission (CIE) activity were synthesized and investigated. 2a-d are almost non-emissive in solutions and amorphous films, but intensely and greenly emissive in crystalline powders and crystals with a quantum yield of 53% and 80%, respectively. The results of X-ray diffraction analysis and theoretical calculation demonstrate that the intramolecular hydrogen bond between C=O and NH groups formed in the excited state of 2 quenches the fluorescence, resulting from the rotation of benzamide groups in their solution and amorphous states. However, it would not happen in their crystalline sates for the locked conformation. Thus, the formation and inhibition of the hydrogen bonding in the excited state may be responsible for their CIE activity. Interestingly, the florescence of the 2d solid can be switched between on/off states by external stimuli including grind, heat, solvent vapor, and acid/alkali, which was utilized to develop three kinds of new technologies for rewritable information storage and security ink.
New compounds for inhibiting differentiation of osteoclast and pharmaceutical composition comprising thereof
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Paragraph 0202, (2014/02/16)
New compounds and pharmaceutical compositions comprising active ingredients having inhibition effects on osteoclast differentiation are provided. The pharmaceutical compositions comprising the new compounds can be used as medicines for treating metabolic bone diseases such as bone metastatic cancer, solid cancer bone metastasis, musculoskeletal complication by solid cancer bone metastasis, hypercalcemia by malignant tumor, multiple myeloma, primary bone tumor, osteoporosis, rheumatoid arthritis, osteoarthritis, periodontal disease, inflammatory resorption of alveolar bone, inflammatory resorption of bone, and Paget's disease.
CuCl-catalyzed radical cyclisation of N-α-perchloroacyl-ketene-N,S- acetals: A new way to prepare disubstituted maleic anhydrides
Cornia, Andrea,Felluga, Fulvia,Frenna, Vincenzo,Ghelfi, Franco,Parsons, Andrew F.,Pattarozzi, Mariella,Roncaglia, Fabrizio,Spinelli, Domenico
experimental part, p. 5863 - 5881 (2012/09/22)
The copper-catalyzed radical cyclization (RC) of N-α-perchloroacyl cyclic ketene-N,X(X=O, NR, S)-acetals was studied. While the RC of N-acyl ketene-N,O-acetals was unsuccessful, the 5-endo cyclization of the other ketene acetals provided much better results, with the following order of cyclization efficiency: hexa-atomic cyclic ketene-N,NR-acetalspenta-atomic cyclic ketene-N,S-acetalshexa-atomic cyclic ketene-N,S-acetals. Invariably the catalytic cycle begins with the formation of a carbamoyl methyl radical. This leads to a cascade of reactions, including a radical polar crossover step, which ends with the formation of the maleimide nucleus, or precursors of this. Products from the RC of the hexa-atomic cyclic ketene-N,S-acetals, were efficiently transformed into disubstituted maleic anhydrides.
New heterocycles of 2,3-diaryl-substituted maleic hydrazides
Shih, Hsiencheng,Shih, Renshuay J.,Carson, Dennis A.
experimental part, p. 1243 - 1250 (2012/01/04)
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
Synthesis and PGE2 production inhibition of 1H-furan-2,5-dione and 1H-pyrrole-2,5-dione derivatives
Moon, Jong Taik,Jeon, Ji Young,Park, Hang Ah,Noh, Young-Soo,Lee, Kyung-Tae,Kim, Jungahn,Choo, Dong Joon,Lee, Jae Yeol
scheme or table, p. 734 - 737 (2010/06/22)
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.
