- Redox-Mediated Decarboxylative Photo-Phenylselenenylation of N-Acyloxyphthalimides
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Decarboxylative phenylselenenylation of N-acyloxyphthalimides by visible light irradiation in aqueous solvents using catalytic amount of Ru(bpy)3Cl2 as a sensitizer in the presence of one equivalent of BNAH and 0.5 equivalent of diphenyl diselenide effici
- Okada, Keiji,Okubo, Katsura,Morita, Naoto,Oda, Masaji
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- Exploratory studies probing the intermediacy of azomethine ylides in the photochemistry of N-phthaloyl derivatives of α-amino acids and β-amino alcohols
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Exploratory photochemical studies with N-phthaloyl derivatives of glutamic acid, aspartic acid, serine, threonine and analogous carboxylic acids and alcohols have been conducted to determine the generality of azomethine ylide forming decarboxylation and retro-aldol fragmentation reactions. Preferences in the competition between these excited state reaction pathways have been determined by studies with phthalimides which contain both α-amino acid and β-aminoethanol groups.
- Yoon, Ung Chan,Lee, Chan Woo,Oh, Sun Wha,Mariano, Patrick S.
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- Utilization of cyanoacetohydrazide and 2-(1,3-dioxoisoindolin-2-yl) acetyl chloride in the synthesis of some novel anti-proliferative heterocyclic compounds
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Owing to its high reactivity and commercial availability, 2-cyanoacetohydrazide can be utilized as a versatile and appropriate intermediate for synthesis of a broad variety of heterocyclic compounds. Thus, 2-cyanoacetohydrazide and 2-(1,3-dioxoisoindolin-2-yl) acetyl chloride were used as starting materials for construction of new heterocyclic compounds bearing 1,3-dioxoisoindoline moiety. The newly synthesized compounds were recognized by elemental analyses and spectral data (IR, 1H-NMR, and 13C-NMR spectra). The synthesized compounds were screened for their anti-proliferative activity against two human epithelial cell lines; breast (MCF-7) and liver (HepG2) as well as to normal fibroblasts (WI-38). The data showed distinctly that compounds 1 and 12 presented promising in-vitro anti-proliferative activity against two cell lines (MCF-7 and HepG2) without harming normal fibroblasts.
- Hekal, Mohamed H.,Ali, Yasmeen M.,Abu El-Azm, Fatma S. M.
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- Spectroscopic and analysis of the hydrolytic process of folpet and its interaction with DNA
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Hydrolysis of the pesticide folpet [N-(trichloromethylthio) phthalimide] in aqueous solution in the absence or presence of calf thymus DNA (ctDNA) was investigated using UV-Vis absorption spectroscopy, and the interactions of folpet and its hydrolyzates with ctDNA were determined by fluorescence and circular dichroism spectroscopy, coupled with viscosity and melting temperature measurements. The absorption spectra data was further analyzed by alternate least squares, a chemometrics method, and the concentration profiles of the reacting species (folpet, unstable intermediate, phthalimide and phthalic acid) and their pure component spectra were simultaneously extracted to monitor the hydrolytic process. It was found that the hydrolytic process consists of at least two steps, generation of an unstable intermediate and production of its end hydrolyzates, phthalimide and phthalic acid. Addition of ctDNA significantly affects the hydrolysis of folpet. The results from the competitive binding with intercalator ethidium bromide, ctDNA melting and viscosity measurements, and circular dichroism studies indicate that folpet and the intermediate can intercalate into the double-helix of DNA, phthalic acid is bound to DNA by a partial intercalation, while phthalimide does not show binding to ctDNA. Moreover, the binding of folpet (or the intermediate) and phthalic acid to ctDNA induced structural changes of the DNA.
- Zhang, Yepeng,Zhang, Guowen
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- Investigations of reactions of selected azaarenes with radicals in water. 2. Chlorine and bromine radicals
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The halogen radicals that react with azaarenes are produced by the photooxidation of halogenide anions with hydroxyl and sulfate radicals and exist as complexes of the radical and the respective halogenide anion in the aqueous phase. The main reaction products of the reactions are identified, and in the case of the bromine radicals, the second order rate constants are determined. Oxidation takes place according to the different redox potentials of the two reactants and is especially observed for chlorine radicals. A typical product spectrum comparable with that in reactions with hydroxyl and sulfate radicals has been found. The formation of some oxidation products in reactions of bromine radicals is in contradistinction to the oxidation potentials of the azaarenes and can be understood only by the reaction of their excited states. The halogenation is the main reaction of the azaarenes. Halogenation products of both, the benzene and the pyridine/diazine rings, have been found. The halogenation of the pyridine/diazine ring again requires the reaction of excited states. The majority of derivatives is halogenated in substitution reactions, but in the reaction of benzo[h]quinoline, addition is also observed. The resonance energy per electron is responsible for the change in the halogenation mechanism from substitution to addition.
- Beitz, Toralf,Bechmann, Wolfgang,Mitzner, Rolf
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- Photochemical Chlorodecarboxylation via an Electron Transfer Mechanism
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A new method of chlorodecarboxylation of carboxylic acids via N-acyloxyphthalimides is developed; the reaction proceeds upon irradiation of N-acyloxyphthalimides in the presence of 1,4-diazabicyclooctane in ButOH-CCl4-H2O (53:42:5 v/v) in moderate to high yields.
- Okada, Keiji,Okamoto, Kazushige,Oda, Masaji
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- Use of Standard Addition to Quantify in Situ FTIR Reaction Data
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FTIR spectroscopy is a common in situ reaction monitoring technique used in modern academic and industrial environments. The FTIR signals collected during the course of a reaction are proportional to the concentration of the reaction components but not intrinsically quantitative. To make FTIR data quantitative, precalibration or offline analyses of reaction samples are required, which diminishes the unique benefits of in situ reaction monitoring techniques. Herein, we report the use of standard addition as a convenient method to obtain quantitative FTIR data.
- Hutchinson, George,Welsh, Calum D. M.,Burés, Jordi
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- Electrochemical reduction of N,N′-thiobisphthalimide and N,N′-dithiobisphthalimide: Ejection of diatomic sulfur through an autocatalytic mechanism
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The electrochemical reduction of N,N′-dithiobisphthalimide and N,N′-thiobisphthalimide is investigated using electrochemical techniques and theoretical calculations. The results are rationalized using adequate electron transfer theories. The reduction leads to the ejection of diatomic sulfur and involves an interesting autocatalytic mechanism. This mechanism is dependent on the concentration of the initial compound and the cyclic voltammetric scan rate. The starting material is reduced both at the electrode and through homogeneous electron transfer from the produced sulfur. The initial electron transfer follows a stepwise mechanism involving the formation of the corresponding radical anion. This is supported by both the electrochemical data and the theoretical calculation results. The radical anion of the N,N′-dithiobisphthalimide dissociates through cleavage of the N-S chemical bond and not the S-S chemical bond. Application of the extension of the dissociative electron transfer theory to the dissociation of radical anions shows that the N-S chemical bond dissociates despite being stronger than the S-S chemical bond. This is due to the large difference in the oxidation potentials of the two potential anions (the phthalimidyl anion and the phthalimidyl thiyl anion). The electrochemical reduction of N,N′-thiobisphthalimide involves the intermediate formation of N,N′-dithiobisphthalimide and hence the autocatalytic process is less efficient.
- Hamed, Emad M.,Koczkur, Kallum M.,Houmam, Abdelaziz
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- Oxidative C-O cross-coupling of 1,3-dicarbonyl compounds and their heteroanalogues with N-substituted hydroxamic acids and N-hydroxyimides
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The oxidative C-O cross-coupling of 1,3-dicarbonyl compounds and their heteroanalogues, 2-substituted malononitriles and cyanoacetic esters, with N-substituted hydroxamic acids and N-hydroxy- imides was realized. The best results were obtained with the use of manganese (III) acetate [Mn (OAc) 3] or the cobalt(II) acetate catalyst [Co (OAc)2cat.]/ potassium permanganate [KMnO4] system as the oxidant. The synthesis can be scaled up to gram quantities of coupling products; yields are 30-94%. The reaction proceeds via a radical mechanism through the formation of nitroxyl radicals from N-substituted hydroxamic acids and N-hydroxyimides.
- Terent'Ev, Alexander O.,Krylov, Igor B.,Timofeev, Vladimir P.,Starikova, Zoya A.,Merkulova, Valentina M.,Ilovaisky, Alexey I.,Nikishin, Gennady I.
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- Photoinduced electron-transfer chemistry of the bielectrophoric N-phthaloyl derivatives of the amino acids tyrosine: Histidine and tryptophan
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The photochemistry of phthalimide derivatives of the electron-rich amino acids tyrosine, histidine and tryptophan 8-10 was studied with respect to photoinduced electron-transfer (PET)induced decarboxylation and Norrish II bond cleavage. Whereas exclusive photodecarboxylation of the tyrosine substrate 8 was observed, the histidine compound 9 resulted in a mixture of histamine and preferential Norrish cleavage. The tryptophan derivative 10 is photochemically inert and shows preferential decarboxylation only when induced by intermolecular PET.
- Griesbeck, Axel G.,Neudoerfl, Joerg,Kiff, Alan De
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- Incorporation of molecular nitrogen into organic compounds. Titanium catalyzed nitrogenation
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Incorporation of molecular nitrogen into organic compounds was realized using a catalytic amount of TiCl4 in the presence of excess TMSCl and Li under nitrogen.
- Kawaguchi, Mami,Hamaoka, Shin-Ichi,Mori, Miwako
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- Methyl esters of 2-(N-hydroxycarbamimidoyl)benzoyl-substituted α-amino acids as promising building blocks in peptidomimetic synthesis: a comparative study
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Abstract: An efficient and simple synthetic protocol for the synthesis of a number methyl esters of 2-(N-hydroxycarbamimidoyl)benzoyl-substituted (S)-α-amino acids via subsequent coupling and hydroxyamination of 2-cyanobenzamide derivatives has been developed. Comparative analysis of three pseudopeptide series based on 2-cyano- and 2-amidoxime-substituted benzoic acid and its pyridine and pyrazine counterparts has been provided and it has revealed a practical advantage of the benzoic acid derivatives due to their greater availability. The impact of the nitrogen atom in the aromatic ring on the trans/cis-amide equilibrium in the proline derivatives is discussed. Graphical abstract: [Figure not available: see fulltext.]
- Tkachuk, Volodymyr A.,Hordiyenko, Olga V.,Omelchenko, Irina V.,Medviediev, Volodomir V.,Arrault, Axelle
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- Imidation of cyclic carboxylic anhydrides under microwave irradiation
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Efficient and facile conversion of cyclic carboxylic anhydrides to corresponding imides with formamide under microwave irradiation is described.
- Peng,Song,Qian
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- Dual linker with a reference cleavage site for information rich analysis of polymer-supported transformations
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Two dual linker systems with specific reference cleavage sites were designed and synthesized to accelerate and simplify development and optimization of reaction conditions for solid-phase synthesis. The dual linker allows simple evaluation of cleavage rate of polymer-supported compounds from the linker and, at the same time, ensures that all resin-bound components are cleaved from the solid support. The dual linker 4 was assembled from two Wang linkers connected by a three carbon spacer. The linker 9 was synthesized using the PAL and HMPB linkers.
- Krchňák, Viktor,Slough, Greg A.
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- A facile and convenient synthesis of 1H-isoindole-1,3(2H)-diones
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A facile synthesis of 1H-isoindole-1,3(2H)-diones (3a-h) has been developed by the reaction of the corresponding anhydrides (1a-h) with potassium cyanate (4a) or sodium thiocyanate (4b). The reactions were carried out in neutral media under reflux or under microwave irradiation without use of catalyst. Good to excellent yields of the products were obtained in high purity with very simple work-up.{A figure is presented}.
- Nikpour, Farzad,Kazemi, Samira,Sheikh, Davood
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- An expedient and convenient approach for one-pot synthesis of 1H-isoindole-1,3(2H)-diones
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An easy and expedient method for the one-pot synthesis of 1H-isoindole-1,3(2H)-diones has been developed by the reaction of the corresponding cyclic anhydrides with guanidinium chloride as a nitrogen source in the presence of FeCl3 as a catalyst under mild reaction conditions.
- Ekhtiari, Zeinab,Havasi, Forugh,Nikpour, Farzad
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- Biotransformations of anthranilic acid and phthalimide to potent antihyperlipidemic alkaloids by the marine-derived fungus Scedosporium apiospermum F41-1
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A new diphenylamine derivative, scediphenylamine A (1), together with six phthalimide derivatives (2–7) and ten other known compounds (8–17) were obtained from the marine-derived fungus Scedosporium apiospermum F41-1 fed with synthetically prepared anthranilic acid and phthalimide. The structure and absolute configuration of the new compound were determined by HRMS, NMR, and X-ray crystallography. Evaluation of their lipid-lowering effect in 3T3-L1 adipocytes showed that scediphenylamine A (1), N-phthaloyl-tryptophan-methyl ester (4), 5-(1,3-dioxoisoindolin-2-yl) pentanamide (5), perlolyrine (10) and flazine (11) significantly reduced triglyceride level in 3T3-L1 cells by inhibiting adipogenic differentiation and synthesis with the EC50 values of 4.39, 2.79, 3.76, 0.09, and 4.52 μM, respectively. Among them, perlolyrine (10) showed the most potent activity, making it a candidate for further development as a potential agent to treat hyperlipidemia.
- Chen, Pei-Nan,Hao, Meng-Jiao,Li, Hou-Jin,Xu, Jun,Mahmud, Taifo,Lan, Wen-Jian
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- Visible-light-promoted radical alkylation/cyclization of allylic amide with N-hydroxyphthalimide ester: Synthesis of oxazolines
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An efficient photocatalytic alkylation/cyclization of allylic amide with N-hydroxyphthalimide ester has been developed. The transformation is taken advantage of alkyl radicals to attack allylic amide with the assist of inexpensive rose bengal as photocatalyst to prepare a series of alkyl substituted oxazolines in moderate to excellent yields. High regioselectivity, operational safety, mild conditions and excellent substrate generality give this protocol broad application prospects.
- Ding, Hao,Huang, Panyi,Jin, Can,Su, Weike,Sun, Bin,Yan, Zhiyang,Zhao, Haiyun
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supporting information
(2021/10/29)
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- Synthesis of N-unsubstituted cyclic imides from anhydride with urea in deep eutectic solvent (DES) choline chloride/urea
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N-Unsubstituted cyclic imides were readily synthesized in deep eutectic solvent (DES) choline chloride (ChCl)/urea from anhydrides with urea. Urea serves as both a DES component and a nitrogen source, which endows the protocol with advantages of smooth reaction, easy separation of products, simple recovery and recycling of ChCl/urea.
- Liu, Luxiao,Zhang, Hong-Yu,Yin, Guohui,Zhang, Yuecheng,Zhao, Jiquan
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p. 1351 - 1357
(2019/11/19)
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- N-Chlorination-induced, oxidative ring contraction of 1,4-dimethoxyphthalazines
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A rarely explored oxidative ring contraction of electron-rich 1,2-diazine is described. Upon treatment with an electrophilic chlorinating reagent (TCICA), 1,4-dimethoxyphthalazines undergo an N-chlorination-induced ring contraction that is accompanied by the loss of one nitrogen atom. The scope of this unusual reactivity was examined with a range of 1,4-dimethoxyphthalazine derivatives. In addition, a mechanism proceeding via a bicyclic species was proposed on the basis of an isolated reaction intermediate and DFT calculations.
- Im, Jeong Kyun,Yang, ByeongDo,Jeong, Ilju,Choi, Jun-Ho,Chung, Won-jin
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- Dual Parasiticidal Activities of Phthalimides: Synthesis and Biological Profile against Trypanosoma cruzi and Plasmodium falciparum
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Chagas disease and malaria are two neglected tropical diseases (NTDs) that prevail in tropical and subtropical regions in 149 countries. Chagas is also present in Europe, the US and Australia due to immigration of asymptomatic infected individuals. In the absence of an effective vaccine, the control of both diseases relies on chemotherapy. However, the emergence of parasite drug resistance is rendering currently available drugs obsolete. Hence, it is crucial to develop new molecules. Phthalimides, thiosemicarbazones, and 1,3-thiazoles have been used as scaffolds to obtain antiplasmodial and anti-Trypanosoma cruzi agents. Herein we present the synthesis of 24 phthalimido-thiosemicarbazones (3 a–x) and 14 phthalimido-thiazoles (4 a–n) and the corresponding biological activity against T. cruzi, Plasmodium falciparum, and cytotoxicity against mammalian cell lines. Some of these compounds showed potent inhibition of T. cruzi at low cytotoxic concentrations in RAW 264.7 cells. The most active compounds, 3 t (IC50=3.60 μM), 3 h (IC50=3.75 μM), and 4 j (IC50=4.48 μM), were more active than the control drug benznidazole (IC50=14.6 μM). Overall, the phthalimido-thiosemicarbazone derivatives were more potent than phthalimido-thiazole derivatives against T. cruzi. Flow cytometry assay data showed that compound 4 j was able to induce necrosis and apoptosis in trypomastigotes. Analysis by scanning electron microscopy showed that T. cruzi trypomastigote cells treated with compounds 3 h, 3 t, and 4 j at IC50 concentrations promoted changes in the shape, flagella, and surface of the parasite body similar to those observed in benznidazole-treated cells. The compounds with the highest antimalarial activity were the phthalimido-thiazoles 4 l (IC50=1.2 μM), 4 m (IC50=1.7 μM), and 4 n (IC50=2.4 μM). Together, these data revealed that phthalimido derivatives possess a dual antiparasitic profile with potential effects against T. cruzi and lead-like characteristics.
- Teixeira de Moraes Gomes, Paulo André,Veríssimo de Oliveira Cardoso, Marcos,dos Santos, Ignes Regina,Amaro de Sousa, Fabiano,da Concei??o, Juliana Maria,Gouveia de Melo Silva, Vanessa,Duarte, Denise,Pereira, Raquel,Oliveira, Rafael,Nogueira, Fátima,Alves, Luiz Carlos,Brayner, Fabio André,da Silva Santos, Aline Caroline,Rêgo Alves Pereira, Valéria,Lima Leite, Ana Cristina
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p. 2164 - 2175
(2020/10/21)
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- Decarboxylative Amination: Diazirines as Single and Double Electrophilic Nitrogen Transfer Reagents
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The ubiquity of nitrogen-containing small molecules in medicine necessitates the continued search for improved methods for C-N bond formation. Electrophilic amination often requires a disparate toolkit of reagents whose selection depends on the specific structure and functionality of the substrate to be aminated. Further, many of these reagents are challenging to handle, engage in undesired side reactions, and function only within a narrow scope. Here we report the use of diazirines as practical reagents for the decarboxylative amination of simple and complex redox-active esters. The diaziridines thus produced are readily diversifiable to amines, hydrazines, and nitrogen-containing heterocycles in one step. The reaction has also been applied in fluorous phase synthesis with a perfluorinated diazirine.
- Chandrachud, Preeti P.,Wojtas, Lukasz,Lopchuk, Justin M.
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supporting information
p. 21743 - 21750
(2021/01/11)
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- Intramolecular Reductive Cyclization of o-Nitroarenes via Biradical Recombination
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A visible-light-induced/thiourea-mediated intramolecular cyclization of o-nitroarenes under mild conditions is realized for the first time, which provides an efficient and environmentally friendly way to access pharmaceutical relevant quinazolinone derivatives. The reaction can be easily extended to gram level by using a continuous-flow setup with high efficiency. Mechanistic investigation including control experiments, transient fluorescence, UV-vis spectra, and DFT calculations suggests that the formation of active biradical intermediates via intramolecular single electron transfer (SET) is key stage in the catalytic cycle.
- Lu, Cong,Su, Zhishan,Jing, Dong,Jin, Songyang,Xie, Lijuan,Li, Liangrui,Zheng, Ke
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supporting information
p. 1438 - 1443
(2019/03/07)
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- Metal-Free Synthesis of Polycyclic Quinazolinones Enabled by a (NH4)2S2O8-Promoted Intramolecular Oxidative Cyclization
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An efficient metal-free, (NH4)2S2O8 mediated intramolecular oxidative cyclization for the construction of polycyclic heterocycles was disclosed. A series of polycyclic quinazolinone derivatives with good functional group tolerance were obtained in high yields. The natural products tryptanthrin and rutaecarpine, as well as their derivatives, were easily synthesized by this strategy. A preliminary mechanism study suggested the carbon-centered radical was involved in the catalytic cycle.
- Xie, Lijuan,Lu, Cong,Jing, Dong,Ou, Xinrui,Zheng, Ke
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supporting information
p. 3649 - 3653
(2019/06/04)
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- PPh3/I2/HCOOH: An efficient CO source for the synthesis of phthalimides
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A straightforward and general method has been developed for the synthesis of phthalimide derivatives from 2-iodobenzamides and PPh3/I2/HCOOH in the presence of a catalytic amount of Pd(OAc)2. The reaction results demonstrate that PPh3/I2/HCOOH is a facile, efficient and safe CO source. The whole process is carried out in toluene at 80 °C and furnishes the desired products in good to excellent yields.
- Wang, Yingying,Zhou, Yang,Lei, Min,Hou, Jinjun,Jin, Qinghao,Guo, Dean,Wu, Wanying
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supporting information
p. 1180 - 1185
(2019/01/26)
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- Synthesis method of anthranilic acid
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The invention relates to a synthesis method of anthranilic acid. The synthesis method comprises the following steps: (1), putting phthalic anhydride and urea into a reaction container, raising the temperature to 140 DEG C, and stirring; (2), after reaction, adding water, and pulping; (3), adding glacial acetic acid and halogen; (4), stirring at room temperature, reacting for three hours, then filtering to obtain a solid, and putting a mother solution into the next batch of a reaction solution; (5), putting the solid into liquid caustic soda, and stirring at room temperature; (6), adding hydrochloric acid into the reaction solution to adjust the pH to 3-4, and separating out a large amount of solid; and (7), filtering and drying to obtain the product anthranilic acid. The synthesis method has the beneficial effects as follows: a halogenating reaction is directly performed on the halogen and phthalamide, and a reaction solvent can be repeatedly used, so that the halogen utilization rateis very high; use of large amounts of acid and alkali is avoided and generation of large amounts of waste salt and waste water is also avoided; and in addition, the waste water has a COD value of 2,000 or below, so that the environmental pollution is very low and the synthesis method is suitable for industrial production.
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Paragraph 0016
(2018/06/26)
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- Grinding imidation of anhydrides on smectite clays as recyclable and heterogeneous catalysts under solvent-free conditions
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Imidation of various anhydrides employing solvent-free grindstone technique using smectite clays as recyclable and green catalysts was examined and obtained excellent yields.
- Marvi, Omid
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p. 3501 - 3504
(2017/08/14)
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- A Novel Green Synthesis of Thalidomide and Analogs
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Thalidomide and its derivatives are currently under investigation for their antiangiogenic, immunomodulative, and anticancer properties. Current methods used to synthesize these compounds involve multiple steps and extensive workup procedures. Described herein is an efficient microwave irradiation green synthesis method that allows preparation of thalidomide and its analogs in a one-pot multicomponent synthesis system. The multicomponent synthesis system developed involves an array of cyclic anhydrides, glutamic acid, and ammonium chloride in the presence of catalytic amounts of 4-N,N-dimethylaminopyridine (DMAP) to produce thalidomide and structurally related compounds within minutes in good isolated yields.
- Benjamin, Ellis,Hijji, Yousef M.
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- Direct Synthesis of Cyclic Imides from Carboxylic Anhydrides and Amines by Nb2O5 as a Water-Tolerant Lewis Acid Catalyst
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In the 20 types of heterogeneous and homogenous catalysts screened, Nb2O5 showed the highest activity for the synthesis of N-phenylsuccinimide by dehydrative condensation of succinic anhydride and aniline. Nb2O5 was used in the direct imidation of a wide range of carboxylic anhydrides with NH3 or amines with various functional groups and could be reused. Kinetic studies showed that the Lewis acid Nb2O5 catalyst was more water tolerant than both the Lewis acidic oxide TiO2 and the homogeneous Lewis acid ZrCl4, which resulted in higher yields of imides through the use of Nb2O5. Int-imidation tactics: A general method for the direct synthesis of cyclic imides from cyclic anhydrides with amines (or ammonia) under solvent-free conditions is reported. Kinetic studies indicate that the Lewis acid sites of Nb2O5 are highly water tolerant, which results in high catalytic activity for imidation even in the presence of water formed during the reaction. The catalyst can be recovered and reused four times without a marked decrease in yield.
- Ali, Md. A.,Moromi, Sondomoyee K.,Touchy, Abeda S.,Shimizu, Ken-Ichi
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p. 891 - 894
(2016/03/15)
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- Experimental study on seawater applications in organic reactions
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Background: Total water resources account for only 2.5% of freshwater on earth, and only 1% of total water resources can be exploited by humans. The development of practical methods of seawater desalination and comprehensive utilization technology can help address the shortage of freshwater resources in the world, and achieve sustainable use of water resources to ensure sustainable development in a society. Direct seawater utilization currently involves industrial cooling water, water for agricultural irrigation, and flushing water. Applications in aqueous phase organic reactions, particularly the direct use of seawater in industrial organic synthesis reactions, are seldom reported. Methods: we used seawater instead of freshwater in selected basic organic chemical reactions. The application of seawater in aqueous phase organic reactions was systematically investigated. Six types of reactions were studied using freshwater and seawater, namely, preparation of acetanilide, synthesis of mandelic acid, Cannizzaro reaction, Hofmann degradation reaction, preparation of quinazolin-4-one, and preparation of adipic acid. Results: Seven organic compounds were produced. Results show that some organic reactions could directly use seawater or treated seawater as an alternative to freshwater. The yields of the reactions using seawater could be compared with literature values, or were even better than literature values. Conclusion: This research provides new opportunities for the comprehensive utilization of seawater. Some organic reactions could directly use seawater or treated seawater instead of freshwater. The use of seawater instead of freshwater for organic reactions in industrial production may greatly conserve freshwater resources and protect the environment.
- Liu, Gang,Qiu, Mingxiang,Sun, Lin,Wen, Quanwu,Xu, Shengguang,Wang, Xuyuan,Wang, Peng
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- Preparation method of high yield isoluminol luminescent reagent
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The invention discloses a preparation method of a high yield isoluminol luminescent reagent. According to the method, the step (1) adopts a microwave preparation method, the reaction time is 5min, and the microwave method can speed up reaction, in step (2), when first pumping filtration of the reaction solution ends, the product is taken out and put into 0.2kg of ice water to conduct stirring and pumping filtration, washing and pumping filtration are carried out repeatedly 4 times, and repeated pumping washing can improve the product purity, a 4-nitrophthalimide product of the step (2) is finally subjected to recrystallization with 300mL of analytically pure, i.e. anhydrous ethanol so as to obtain a refined product, use of the ethanol as the extracting agent can improve the product purity, the hydrazine hydrate used in step (3) has purity of 85%, and the purity of ordinary industrial hydrazine hydrate is 40-80%, by using higher purity hydrazine hydrate in the invention, the product yield can be increased, and the cooling temperature of step (4) is -3DEG C, the product can crystallize rapidly under the temperature, thus ensuring the purity and yield of the product.
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Paragraph 0032; 0033
(2017/06/02)
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- Synthesis, structural and antioxidant studies of some novel N-ethyl phthalimide esters
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A series of N-ethyl phthalimide esters 4(a-n) were synthesized and characterized by spectroscopic studies. Further, the molecular structure of majority of compounds were analysed by single crystal X-ray diffraction studies. The X-ray analysis revealed the importance of substituents on the crystal stability and molecular packing. All the synthesized compounds were tested for in vitro antioxidant activity by DPPH radical scavenging, FRAP and CUPRAC methods. Few of them have shown good antioxidant activity.
- Kumar, C.S. Chidan,Loh, Wan-Sin,Chandraju, Siddegowda,Win, Yip-Foo,Tan, Weng Kang,Quah, Ching Kheng,Fun, Hoong-Kun
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- A phthalimidation protocol that follows protein defined parameters
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This work outlines the first phthalimidation protocol suitable for protein labeling and performed in aqueous media at room temperature and neutral pH with no catalyst or co-reagent required. The methodology is suitable for a range of amines and its efficiency was determined with chemoselective and site-selective protein labeling. This journal is
- Singudas, Rohith,Adusumalli, Srinivasa Rao,Joshi, Pralhad Namdev,Rai, Vishal
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supporting information
p. 473 - 476
(2015/01/09)
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- Copper-catalyzed aerobic C-C bond cleavage of lactols with N-hydroxy phthalimide for synthesis of lactones
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The transformation of cyclic hemiacetals (lactols) into lactones has been achieved by Cu-catalyzed aerobic C-C bond cleavage in the presence of N-hydroxy phthalimide (NHPI). The present process is composed of a multistep sequence including a) formation of exo-cyclic enol ethers by dehydration; b) addition of phthalimide N-oxyl radical to the enol ethers followed by trapping of the resulting C-radicals with molecular oxygen to form peroxy radicals; c) reductive generation of oxy radicals and subsequent β-radical fragmentation to generate lactones.
- Tnay, Ya Lin,Chiba, Shunsuke
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supporting information
p. 873 - 877
(2015/04/14)
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- Choline chloride based eutectic solvent: An efficient and reusable solvent system for the synthesis of primary amides from aldehydes and from nitriles
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Choline chloride: a 2ZnCl2 based deep eutectic solvent was found to be a simple, green, efficient and new solvent system for the preparation of primary amides from aldehydes. The same catalytic system is also applicable for the preparation of amides from nitriles. Good to excellent yields of primary amides were obtained in both these transformations.
- Patil, Umakant B.,Singh, Abhilash S.,Nagarkar, Jayashree M.
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p. 1102 - 1106
(2014/01/06)
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- Ammonolysis of anilides promoted by ethylene glycol and phosphoric acid
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Ethylene glycol (EG) and phosphoric acid have been found to promote the ammonolysis of a variety of diverse anilides as well as N-aryl carbamate, phthalimide, and urea substrates in the absence of transition metals or other Lewis acid promoters.
- Stephenson, Nickeisha A.,Gellman, Samuel H.,Stahl, Shannon S.
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p. 46840 - 46843
(2014/12/10)
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- Synthesis and evaluation of antibacterial activity of water-soluble copper, nickel and zinc tetra (n-carbonylacrylic) aminephthalocyanines
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Water-soluble copper, nickel, and zinc tetra (n-carbonylacrylic) aminephthalocyanines were synthesized with an aim to evaluate their role as therapeutic materials. They were characterized by UV-Vis spectrophotometer, infra-red spectra, elemental analysis, nuclear magnetic resonance, and thermogravimetry. Efforts were made to optimize the synthesis of intermediates and final products. Photoluminescence studies were carried out on these compounds. The investigation of antibacterial activity of these aqueous soluble phthalocyanines was carried out on Staphylococcus citreus, Serratia marcescens, Proteus vulgaris, Bacillus subtilis, and Pseudomonas fluorescence, showed good inhibitory activity.
- Pavaskar,Patil,Furtado,Salker
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p. 4300 - 4307
(2013/09/02)
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- Reactivity of ortho-palladated benzamides toward CO, isocyanides, and alkynes. synthesis of functionalized isoindolin-1-ones and 4,5-disubstituted benzo[ c ]azepine-1,3-diones
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Aryl palladium complexes [Pd{C6H4C(O)NRR′-2} I(tmeda)] [NRR′ = NH2 (1a), NHMe (1b), NMe2 (1c); tmeda = N,N,N′,N′-tetramethylethylenediamine] are prepared by oxidative addition of the corresponding 2-iodophenylbenzamides to "Pd(dba)2" ([Pd2(dba)3]·dba; dba = dibenzylideneacetone) in the presence of tmeda. Cationic cyclometalated derivatives [Pd{κ2C,O-C6H4C(O)NRR′- 2}(tmeda)]TfO (2a-c) are obtained by iodide abstraction from the appropriate complex 1 with AgTfO, while the deprotonation of the amide function of 1a or 1b with KOtBu gives the neutral amidate complexes [Pd{κ 2C,N-C6H4C(O)NR-2}(tmeda)] [R = H (3a), Me (3b)]. Complexes 2a,b and 3a,b react with CO under mild conditions to yield phthalimide (4a) or N-methylphthalimide (4b), whereas the reactions of derivatives 1c and 2c with CO are very slow and give N1,N 1,N2,N2-tetramethylphthalamide and phthalic anhydride. The reaction of 1b with 1 equiv of XyNC (Xy = 2,6-dimethylphenyl) or tBuNC affords Pd(0), (tmedaH)I, and 3-(2,6-dimethylphenylimino)-2- methylisoindolin-1-one (5b) or 3-(tert-butylimino)-2-methylisoindolin-1-one (5b′), respectively, while complex 1c reacts with 3 equiv of XyNC to give trans-[Pd{C(i=NXy)C6H4C(O)NMe2-2}I(CNXy) 2] (6). The seven-membered palladacycles [Pd{κ2C,O- C(X)i=C(X′)C6H4C(O)NRR′-2}(tmeda)]TfO [NRR′ = NH2 and X = Ph, X′ = Me (7a); NRR′ = NHMe and X = Ph, X′ = Me (7b), X = X′ = Ph (8b), Et (9b), CO 2Me (10b), X = CO2Me, X′ = Ph (11b), X = CO 2Et, X′ = Ph (12b); NRR′ = NMe2 and X = X′ = Ph (8c), Et (9c)] are obtained from the reactions of 2a-c with alkynes. Treatment of complexes 7a, 7b, 8b, and 9b with CO at room temperature gives the corresponding 2H-benzo[c]azepine-1,3-diones (14), resulting from the insertion of a molecule of CO into the Pd-C bond followed by a C-N reductive coupling. In contrast, the reactions of 11b or 12b with CO in the presence of residual water or 2 equiv of ROH (R = Me, Et) lead to 2-methyl-3- phenylisoindolin-1-one derivatives (15), resulting from a CO insertion followed by an intramolecular aza-Michael addition of the NHMe moiety to the activated vinyl group and subsequent hydrolysis or alcoholysis of the acyl-Pd bond. The neutral complex [Pd(κ2C,O-C14H13O 5)(tmeda)] (18) was synthesized by reacting the cationic derivative 10b with NaOMe in MeOH. Depalladation of 18 gives (E)-4- [methoxy(methoxycarbonyl)methylene]-2-methylisoquinoline-1,3(2H,4H)-dione (19).
- Frutos-Pedreno, Roberto,Gonzalez-Herrero, Pablo,Vicente, Jose,Jones, Peter G.
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p. 4664 - 4676
(2013/09/23)
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- Kinetics and mechanism of the oxidation of 4-Oxo-4-arylbutanoic acids by N-bromophthalimide in aqueous acetic acid medium
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The kinetics of oxidation of a series of substituted 4-oxobutanoic acids (Y-C6H4COCH2CH2COOH: Y = H, OCH 3, CH3, C6H5, Cl, Br or NO 2) by N-bromophthalimide have been studied in aqueous acetic acid medium at 30 C. The total reaction is second-order, first-order each in oxidant and substrate. The oxidation rate increases linearly with [H+], establishing the hypobromous acidium ion, H2O+Br, as the reactive species. A variation in ionic strength has no effect on the reaction rate. The order of reactivity among the studied 4-oxoacids is: 4-methoxy > 4-methyl > 4-phenyl > 4-H > 4-Cl > 4-Br > 3-NO2. The effect of changes on the electronic nature of the substrate reveals that there is a development of positive charge in the transition state. The activation parameters have been computed from Arrhenius and Eyring plots. Based on the kinetic results, a suitable mechanism has been proposed.
- Mohamed Farook,Alhaji,Uduman Mohideen,Seyed Dameen,Mitu, Liviu,Abshana Begam
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p. 1183 - 1193
(2013/07/26)
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- Green oxidative synthesis of primary amides from primary alcohols or aldehydes catalyzed by a cryptomelane-type manganese oxide-based octahedral molecular sieve, OMS-2
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In this study, a new green synthetic route to primary amides, that is, aerobic oxidative amidation of primary alcohols or aldehydes with ammonia, has been developed. In the presence of a cryptomelane-type manganese oxide-based octahedral molecular sieve (OMS-2), various kinds of structurally diverse primary alcohols or aldehydes including aromatic, olefinic, heteroaromatic, and aliphatic ones can be converted into the corresponding primary amides in moderate to high yields (20 examples from primary alcohols and 11 examples from aldehydes). Furthermore, gram-scale amidation is also effective, and the analytically pure primary amides can easily be isolated. The present catalysis by OMS-2 is truly heterogeneous in nature, and the retrieved OMS-2 catalyst can be reused several times (at least 12 times for the amidation of 2-pyridinemethanol). Though the formation rates of the corresponding primary amide are gradually decreased by repeating reuse experiments, OMS-2 can be regenerated by calcination. The present OMS-2-catalyzed amidation of primary alcohols is composed of four relay steps: (i) oxidative dehydrogenation of primary alcohols, (ii) dehydrative condensation of aldehydes with ammonia, (iii) oxidative dehydrogenation of aldimines, and (iv) hydration of nitriles to form the corresponding primary amides. All steps (i)-(iv) can be promoted by the presence of OMS-2. The Royal Society of Chemistry 2013.
- Yamaguchi, Kazuya,Kobayashi, Hiroaki,Wang, Ye,Oishi, Takamichi,Ogasawara, Yoshiyuki,Mizuno, Noritaka
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p. 318 - 327
(2013/03/14)
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- Mechanistic aspects of oxidation of dextrose by N-bromophthalimide in acidic medium: A micellar kinetic study
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Kinetic investigations of oxidation of dextrose by N-bromophthalimide (NBP) in acidic medium in the presence of mercuric(II) acetate as a scavenger have been studied. In both the absence and presence of surfactants, the oxidation kinetics of dextrose by NBP shows a first-order dependence on NBP, fractional order on dextrose, and negative fractional order dependence on sulfuric acid. The determined stoichiometric ratio was 1:1 (dextrose:NBP). The variation of Hg(OAC)2 and phthalimide (reaction product) have an insignificant effect on reaction rate. Effects of surfactants, added acrylonitrile, added salts, and solvent composition variation have been studied. Activation parameters for the reaction have been evaluated from Arrhenius plot by studying the reaction at different temperature. The rate law has been derived on the basis of obtained data. A plausible mechanism has been proposed from the results of kinetic studies, reaction stoichiometry and product analysis. The role of anionic and non-ionic micelle was best explained by the Berezin's model.
- Singh, Minu
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p. 469 - 484
(2013/07/27)
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- Solvent-free synthesis of phthalimide under microwave irradiation and modification of talc with synthesized phthalimide
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A simple and effective procedure for the synthesis of phthalimide had been developed under solvent-free microwave irradiation condition and the structure of the synthesized compound had been characterized by FT-IR, 1H NMR. Morphology and thermal properties of phthalimide synthesized by this solvent-free reaction under microwave irradiation were further investigated by scanning electron microscopy (SEM) and TGA thermal analyzer, respectively. SEM showed the particles of phthalimide were not completely regular, but the most of the phthalimide was rodlike and the average length of the rodlike particles was 1 μ m. At the same time, the optimized geometric structure of phthalimide was carried out by theoretical calculations using the semiempirical method PM3. The results of TGA indicated that decomposition temperature significantly increased with increasing of heating rate and decomposition rate was fast. Upon heating rate of 10 °C/min, phthalimide showed good thermal stability of phthalimide under 150 °C and that the decomposition completed at 250 °C. Finally, the synthesized phthalimide was used to successfully modify the surface of talc.
- Cai, Yan-Hua
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experimental part
p. 481 - 484
(2012/07/28)
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- Intramolecular thermal transformations of N-phthalimidoaziridines: 1,3-dipolar cycloaddition and rearrangements
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The intramolecular thermal cycloaddition of N-phthalimidoaziridines at multiple bonds of substituents with the intermediate formation of azomethine ylides leads to condensed pyrrole derivatives, in which the five-membered ring is adjacent to a five-, six-, or seven-membered ring. Rearrangements, which sometimes become the predominant reactions, compete with cycloaddition. Thus, aziridines with aryl substituents readily isomerize to give imines with a 1,2-shift of the phthalimide group to one of the carbon atoms. Aziridines with one electron-withdrawing substituent probably do not open to give 1,3-dipoles but rather undergo a Cope-type rearrangement involving the three-membered ring and C=O bond of the second substituent. Even in intramolecular reactions, very low activity is found for the cyano group triple bond and aromatic ring bonds as dipolarophiles.
- Kuznetsov,Pan'Kova,Voronin,Vlasenko
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p. 1353 - 1366
(2014/07/21)
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- Hofmann-type rearrangement of imides by in situ generation of imide-hypervalent iodines(III) from iodoarenes
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The Hofmann-type rearrangement of aromatic and aliphatic imides using a hypervalent iodine(III) reagent generated in situ from PhI, m-CPBA, and TsOH·H2O proceeded in the presence of a base in alcohol to provide anthranilic acid derivatives and amino acid derivatives in high yields, respectively. This reaction proceeds through a tandem reaction via alcoholysis followed by a Hofmann rearrangement promoted by the formation of an imide-λ3-iodane intermediate.
- Moriyama, Katsuhiko,Ishida, Kazuma,Togo, Hideo
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scheme or table
p. 946 - 949
(2012/05/05)
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- Design, synthesis, and pharmacological evaluation of novel hybrid compounds to treat sickle cell disease symptoms
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A novel series of thalidomide derivatives (4a-f) designed by molecular hybridization were synthesized and evaluated in vitro and in vivo for their potential use in the oral treatment of sickle cell disease symptoms. Compounds 4a-f demonstrated analgesic, anti-inflammatory, and NO-donor properties. Compounds 4c and 4d were considered promising candidate drugs and were further evaluated in transgenic sickle cell mice to determine their capacity to reduce the levels of the proinflammatory cytokine tumor necrosis factor α (TNFα). Unlike hydroxyurea, the compounds reduced the concentrations of TNFα to levels similar to those induced with the control dexamethasone (300 μMol/kg). These compounds are novel lead drug candidates with multiple beneficial actions in the treatment of sickle cell disease symptoms and offer an alternative to hydroxyurea treatment.
- Dos Santos, Jean Leandro,Lanaro, Carolina,Lima, Ldia Moreira,Gambero, Sheley,Franco-Penteado, Carla Fernanda,Alexandre-Moreira, Magna Suzana,Wade, Marlene,Yerigenahally, Shobha,Kutlar, Abdullah,Meiler, Steffen E.,Costa, Fernando Ferreira,Chung, Manchin
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scheme or table
p. 5811 - 5819
(2011/10/09)
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- Intra- and intermolecular thermal transformations of 2-acyl- and 2-alkoxycarbonyl-N-phthalimidoaziridines
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Heating 2-acyl- and 2-alkoxycarbonyl-N-phthalimidoaziridines leads to substituted oxazoles in 45-65% yield. Only esters of oxazolecarboxylic acids are formed when the aziridine contains acyl and alkoxy groups. The thermolysis of the same aziridines in the presence of N-phenylmaleimide and the dimethyl ester of acetylenedicarboxylic acid gives both oxazoles and the products of 1,3-dipolar cycloaddition from aziridines with two substituents at the carbon atoms but only oxazoles from trisubstituted aziridines.
- Kuznetsov,Voronin
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p. 173 - 181
(2012/01/02)
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- Gas-phase pyrolysis of N-alkoxyphthalimides to functionally substituted aldehydes: Kinetic and mechanistic study
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Flash vacuum Pyrolysis (FVP) of primary N-alkoxyphthalimides at 400-500 C° and 0.02 Torr gave functionally substituted aldehydes. A mechanism of this pyrolytic transformation was proposed based on the kinetic data and product analysis. ARKAT USA, Inc.
- Al-Etaibi, Alya M.,Al-Awadi, Nouria A.,Ibrahim, Maher R.,Ibrahim, Yehia A.
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experimental part
p. 149 - 162
(2010/12/25)
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- Self-assembly of phthalocyanine and polyacrylic acid composite multilayers on cellulose nanofibers
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In this study, a novel nanocomposite multilayers was deposited on the electrospun nanofibrous mats by an electrostatic layer-by-layer (LBL) self-assembly technique. The positively charged water-insoluble 2,9,16,23-tetraaminophthalocyanine copper (CuTaPc) and the negatively charged water-soluble poly(acrylic acid) (PAA) were alternately deposited on the surface of negatively charged nanofibrous cellulose mats. The cationic CuTaPc was synthesized and characterized by UV-Vis and Fourier transform infrared (FT-IR) spectroscopy. The template nanofibrous cellulose mats were obtained from the alkaline hydrolysis of electrospun nanofibrous cellulose acetate mats. The resultant nanofibrous mats were characterized by scanning electron microscopy (SEM) and FT-IR spectroscopy. The SEM images showed that the composite LBL structured films were homogeneously deposited on the surface of the nanofibers. The diameters of nanofibers increased with the number of deposition bilayers. The average thickness of each CuTaPc/PAA bilayer is about 10 nm. Additionally, the FT-IR spectra results also indicated that the CuTaPc and PAA were coated on the nanofibrous cellulose mats.
- Mao, Xue,Ding, Bin,Wang, Moran,Yin, Yanbing
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scheme or table
p. 839 - 844
(2011/11/06)
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- The first experimental demonstration of side chain extension of geoporphyrins in sediments
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To investigate the formation process of high carbon number (>C 32) sedimentary porphyrins, heating experiments of several porphyrins were performed. Chromic acid oxidation of the heating products of protoporphyrin IX dimethyl ester afforded 2-methyl-3-npropylmaleimide as the predominant product among the side-chain extension products formed. On the other hand, saturated substituents of etioporphyrin were also extended on heating to slowly form normal and branched homologs. These results may suggest that the transalkylation of porphyrin side chains proceeds mainly by a regioselective mechanism involving alkyl radical addition to a vinyl group of chlorophylls or their diagenetic products.
- Asahina, Kenta,Asano, Junya,Kumagai, Gen,Satou, Mitsuru,Nomoto, Kouichi,Kashiyama, Yuichiro,Mita, Hajime,Nomoto, Shinya
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body text
p. 1267 - 1269
(2011/02/16)
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- Synthesis of the phosphonoanalogue of benzo[c]pyroglutamic acid
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Phosphonic analogue 1 of benzo[c]pyroglutamic acid was synthesized by three-step synthesis starting from N-tert-butylphtalimide and triethylphosphite. The acid-catalyzed, oxidative cascade conversion of phosphonate 11 to phthalimide and phosphoric acid diethyl ester was observed. A mechanism for this transformation was proposed. Taylor & Francis Group, LLC.
- Kachkovskyi, Georgiy O.,Kolodiazhnyi, Oleg I.
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experimental part
p. 2441 - 2448
(2011/02/25)
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- A cyclic porphyrin trimer as a receptor for fullerenes
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(Equation Presented). A cyclic porphyrin trimer has been synthesized which has a high affinity for fullerenes. It forms 1:1 complexes with C60 and C70 with association constants of 2×106 and 2×108 M-1, respectively, in toluene. Its affinities for C86 and La@C82 are too strong to measure by fluorescence titration. The solvent dependence of the association constants shows that solvation of both the guest and the host influence the binding strength.
- Gil-Ramirez, Guzman,Karlen, Steven D.,Shundo, Atsuomi,Porfyrakis, Kyriakos,Ito, Yasuhiro,Briggs, G. Andrew D.,Morton, John J. L.,Anderson, Harry L.
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supporting information; experimental part
p. 3544 - 3547
(2010/10/02)
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- Tri- and tetrasubstituted N-phthalimidoaziridines in 1,3-dipolar cycloaddition reactions
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The thermal reactions of the 2,2,3-trisubstituted N-phthalimidoaziridine 1a with dimethyl acetylenedicarboxylate (DMAD), thioketones 4a - 4d, and dimethyl azodicarboxylate (5) proceed even at room temperature leading to the five-membered cycloadducts 2a, 6 - 8, and 12, respectively, with retention of the spatial arrangement of the aziridine substituents, in contrast to the expectation based on the conservation of orbital symmetry in concerted reactions. The analogous reactions of the tetrasubstituted phthalimidoaziridine 1b with thioketones at 40° lead to the 1,3-thiazolidine derivatives 10 and 11 as mixtures of diastereoisomers. These unexpected results may be explained by either the isomerization of the intermediate azomethine ylides or a non-concerted stepwise cycloaddition reaction of these ylides with the dipolarophiles. The structures of some adducts have been determined by X-ray crystallography.
- Ushkov, Alexander V.,Kuznetsov, Mikhail A.,Linden, Anthony,Heimgartner, Heinz
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experimental part
p. 847 - 862
(2010/08/06)
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- An efficient InCl3-catalyzed hydration of nitriles to amides: acetaldoxime as an effective water surrogate
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An efficient InCl3-catalyzed hydration protocol of nitriles to amides was developed. The reaction was carried out in toluene at refluxing temperature with the aid of acetaldoxime as an effective water surrogate to produce amides in high yields.
- Kim, Eun Sun,Lee, Hyun Seung,Kim, Sung Hwan,Kim, Jae Nyoung
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scheme or table
p. 1589 - 1591
(2010/04/29)
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- A kinetic study of acid-catalyzed hydrolysis of some arylsulfonyl phthalimides
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The acid-catalyzed hydrolysis of arylsulfonyl phthalimides was studied in aqueous solutions of sulfuric, perchloric, and hydrochloric acid at 35.0 ± 0.1C. Analysis of the data by the excess acidity method and activation parameters, as well as substituent and solvent isotope effects, indicate hydrolysis by an A-2 mechanism at low acidity. At higher acidities, a changeover to an A-1 mechanism is observed.
- Kutuk, Halil,Ozturk, Seyhan
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scheme or table
p. 332 - 340
(2009/09/25)
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- The synthesis of unsubstituted cyclic imides using hydroxylamine under microwave irradiation
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Unsubstituted cyclic imides were synthesized from a series of cyclic anhydrides, hydroxylamine hydrochloride (NH2OH·HCl), and 4-N,N-dimethylamino-pyridine (DMAP, base catalyst) under microwave irradiation in monomode and multimode microwaves. This novel microwave synthesis produced high yields of the unsubstituted cyclic imides for both the monomode (61-81%) and multimode (84-97%) microwaves.
- Benjamin, Ellis,Hijji, Yousef
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p. 157 - 169
(2008/09/17)
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- Novel fluorescent fluorine-boron complexes: Synthesis, crystal structure, photoluminescence, and electrochemistry properties
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(Chemical Equation Presented) Two novel fluorine-boron cored fluorescent complexes were designed and synthesized. These two complexes displayed well-ordered molecular packing, intense fluorescence, and low LUMO levels. The results indicated their potential use as electron-transport materials in electroluminescent (EL) devices.
- Zhou, Ying,Xiao, Yi,Li, Dan,Fu, Meiyan,Qian, Xuhong
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p. 1571 - 1574
(2008/09/17)
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- COMPOSITIONS AND METHODS FOR POLYMER COMPOSITES
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This invention relates to organic salt compositions useful in the preparation of organoclay compositions, polymer-organoclay composite compositions, and methods for the preparation of polymer nanocomposites. In one embodiment, the present invention provides a pyridinium salt having structure XV wherein Ar6, Ar7, and Ar8 are independently C2-C50 aromatic radicals; “b” is a number from 0 to 2; “d” is a number from 0 to 4; R3 and R4 are independently at each occurrence a halogen atom, a C1-C20 aliphatic radical, a C5-C20 cycloaliphatic radical, or a C2-C20 aromatic radical; Z is a bond, a divalent C1-C20 aliphatic radical, a divalent C5-C20 cycloaliphatic radical, a divalent C2-C20 aromatic radical, an oxygen linking group, a sulfur linking group, a SO2 linking group, or a Se linking group; Ar9 is a C10-C200 aromatic radical, or a polymer chain comprising at least one aromatic group; and X? is a charge balancing counterion.
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- Inhibitors of dipeptidyl peptidase 8 and dipeptidyl peptidase 9. Part 2: Isoindoline containing inhibitors
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To obtain selective and potent inhibitors of dipeptidyl peptidases 8 and 9, we synthesized a series of substituted isoindolines as modified analogs of allo-Ile-isoindoline, the reference DPP8/9 inhibitor. The influence of phenyl substituents and different P2 residues on the inhibitors' affinity toward other DPPs and more specifically, their potential to discriminate between DPP8 and DPP9 will be discussed. Within this series compound 8j was shown to be a potent and selective inhibitor of DPP8/9 with low activity toward DPP II.
- Van Goethem, Sebastiaan,Van der Veken, Pieter,Dubois, Veronique,Soroka, Anna,Lambeir, Anne-Marie,Chen, Xin,Haemers, Achiel,Scharpe, Simon,De Meester, Ingrid,Augustyns, Koen
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scheme or table
p. 4159 - 4162
(2009/05/07)
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