- Facile Synthesis of γ-Butenolides and Maleic Anhydrides via Annulation of α-Keto Acids and Triazenyl Alkynes
-
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.
- Bao, Xiaodong,Cui, Sunliang,Jin, Jian,Zeng, Linwei
-
-
- Choline hydroxide promoted sustainable one-pot three-component synthesis of 1H-pyrazolo[1,2-a]pyridazine-2-carbonitriles under solvent-free conditions
-
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.
- Vajekar, Shailesh N.,Shankarling, Ganapati S.
-
supporting information
p. 1147 - 1158
(2020/03/30)
-
- Diarylmaleic anhydrides: unusual organic luminescence, multi-stimuli response and photochromism
-
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
-
p. 2135 - 2141
(2017/03/09)
-
- 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
-
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
-
supporting information
p. 5794 - 5799
(2016/11/06)
-
- Maleimide fused boron-fluorine complexes: Synthesis, photophysical and electrochemical properties
-
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.
-
supporting information
p. 13947 - 13954
(2015/08/18)
-
- Strong CIE activity, multi-stimuli-responsive fluorescence and data storage application of new diphenyl maleimide derivatives
-
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.
- Zheng, Rong,Mei, Xiaofei,Lin, Zhenghuan,Zhao, Yan,Yao, Huimei,Lv, Wei,Ling, Qidan
-
p. 10242 - 10248
(2015/10/12)
-
- New compounds for inhibiting differentiation of osteoclast and pharmaceutical composition comprising thereof
-
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.
- -
-
Paragraph 0202
(2014/02/16)
-
- CuCl-catalyzed radical cyclisation of N-α-perchloroacyl-ketene-N,S- acetals: A new way to prepare disubstituted maleic anhydrides
-
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.
- 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)
-
- New heterocycles of 2,3-diaryl-substituted maleic hydrazides
-
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.
-
experimental part
p. 1243 - 1250
(2012/01/04)
-
- The spermine-bisaryl conjugate as a potent inducer of B- to Z-DNA transition
-
DNA containing alternating purine and pyrimidine repeats has the potential to adopt the Z-DNA structure, one of the well-studied structures besides A- and B-DNA. Despite a number of molecular models that have been proposed to explain the mechanism for B→Z transition, there is continued discussion on the mechanism and physiological role of this transition. In this study, we have found that the bis(2-naphthyl)-maleimide-spermine conjugate (3c) exhibits a remarkable ability to cause the B→Z transition of d(CGCGCG)2 at low salt concentrations. Using isothermal titration calorimetry (ITC) we show that the B→Z transition induced by 3c is both enthalpically and entropically favorable. The ligand might effect the dehydration of B-DNA, which leads to the B→Z transition. Interestingly, an intermediate CD between the B and Z forms was observed in the pH-dependent transition in the presence of the ligand. The unique structure and characteristics of the ligand designed in this investigation will be useful for the study of Z-DNA. From B to Z: The bis(2-naphthyl)maleimide-spermine conjugate shown in the figure exhibits a remarkable ability to cause the B→Z transition of d(CGCGCG)2 at low salt concentrations. A stable intermediate between the B and Z forms was observed in the presence of the ligand at about pH 8.
- Doi, Issei,Tsuji, Genichiro,Kawakami, Kyoko,Nakagawa, Osamu,Taniguchi, Yosuke,Sasaki, Shigeki
-
experimental part
p. 11993 - 11999
(2011/01/12)
-
- Synthesis and PGE2 production inhibition of 1H-furan-2,5-dione and 1H-pyrrole-2,5-dione derivatives
-
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
-
scheme or table
p. 734 - 737
(2010/06/22)
-
- Efficient electrochemical dicarboxylations of arylacetylenes with carbon dioxide using nickel as the cathode
-
The electrochemical dicarboxylation of arylacetylenes with carbon dioxide could be smoothly achieved in an undivided cell using Ni as the cathode and Al as the anode with n-Bu4NBr-DMF as the supporting electrolyte, at a constant current under CO2 pressure of 3 MPa and room temperature in the absence of additional catalysts. The corresponding aryl-maleic anhydrides and 2-arylsuccinic acids were afforded in excellent total yields (82-94%). Under anhydrous conditions, an unsaturated aryl-maleic anhydride as the main product was obtained, while the presence of H2O would lead to the formation of saturated 2-arylsuccinic acids. The results of cyclic voltammetric experiments show that a nickel cathode itself plays the catalytic role in the reduction reaction of arylacetylenes with CO2.
- Yuan, Gao-Qing,Jiang, Huan-Feng,Lin, Chang
-
p. 5866 - 5872
(2008/09/21)
-
- A simple, convenient method for the synthesis of maleic anhydrides from α-keto esters and alkanoic acid anhydrides using the TiCl 4/n-Bu3N reagent system
-
Reaction of α-keto esters with alkanoic acid anhydrides using the TiCl4/n-Bu3N reagent system gives the corresponding maleic anhydrides in 62-95% yields.
- Kishorebabu, Neela,Periasamy, Mariappan
-
p. 2107 - 2109
(2007/10/03)
-
- Synthesis in a stage of N-methoxyindolinones, N-methoxymaleimides and maleic anhydrides starting from α-halogen hydroxamic acids
-
α-Halo hydroxamic acids were used in the synthesis of N-methoxyindolinones, symmetric and dissymmetric N-methoxymaleimides in good yields. The hydrolysis of N-methoxymaleimides constitues a new and good route to maleic anhydrides.
- Boukhris, Sa?d,Souizi, Abdelaziz
-
p. 7455 - 7458
(2007/10/03)
-
- Synthesis of 3,4-diarylsubstituted maleic anhydride/maleimide via unusual oxidative cyclization of phenacyl ester/amide
-
A simple and general method has been developed for the synthesis of 3,4-diarylsubstituted maleic anhydride and maleimide through tandem cyclization and oxidation reaction of phenacyl ester or amide. A wide variety of phenacyl esters or amides was treated with DBU under oxygen atmosphere to give the expected compounds in good to excellent yield. Mechanism of the reaction and application of the methodology have been discussed.
- Pattabiraman, Vijaya Raghavan,Padakanti, Srinivas,Veeramaneni, Venugopal Rao,Pal, Manojit,Yeleswarapu, Koteswar Rao
-
p. 947 - 951
(2007/10/03)
-
- A new access to diarylmaleic anhydrides
-
A new three-step synthesis of diarylmaleic anhydrides 6, starting from 3-aryl-2-hydroxybut-2-enedioates 2, is reported.
- Beccalli, Egle M.,Gelmi, Maria Luisa,Marchesini, Alessandro
-
p. 1421 - 1426
(2007/10/03)
-
- SYNTHESE DE N-AMINO MALEIMIDES ET D'ANHYDRIDES MALEIQUES DISUBSTITUES A PARTIR D'α-HALOGENO HYDRAZIDES. ETUDE DU MECANISME DE LA REACTION.
-
α-Halohydrazides react with 2-aminopyridine to give symmetrically substituted N-aminomaleimides.We have shown that this reaction proceeds through the formation of 4-hydroxyimidazopyridines.This result opens a new route to dissymetrically substituted N-aminomaleimides.The hydrolysis of N-aminomaleimides is a grood route to substituted maleic anhydrides.
- Florac, C.,Baudy-Floc'h, M.,Robert, A.
-
p. 445 - 452
(2007/10/02)
-
- A New Synthetic Route to N-Amino Maleimides
-
N-Amino maleimides have been obtained in good yield through the reaction of α-halohydrazides with N-aminopyridine.
- Florac, Claudie,Baudy-Floc'h, Michele,Robert, Albert
-
p. 1524 - 1525
(2007/10/02)
-
- Ring Transformation of 3,4-Diphenyl-2-furylcarbamoyl Compounds to N-Substituted 3,4-Diphenyl-5-hydroxy-3-pyrrolin-2-ones
-
3,4-Diphenyl-2-furylcarbamoyls (IIIa - e) react with oxygen in benzene at room temperature and in the abscence of catalysts or bases to give 3,4-diphenyl-5-hydroxy-3-pyrrolin-2-ones (Va - e) as main products.Under the same conditions, treatment of 3,4-diphenyl-2-furyl isocyanate (II) with an excess of various amines resulted in a clean autoxidation reaction to give Ve - h and diphenylmaleimides (XIIa - d) in a ratio of about 1:1. 3-Hydroxyphenantropyrrolin-1-ones (XIIIa - e) were prepared by the photocyclization of Va - e.
- Yakushijin, Kenichi,Kozuka, Masamichi,Furukawa, Hiroshi
-
p. 2178 - 2184
(2007/10/02)
-