Synthesis of 3-Amino-7-(N,N-Dimethylamino)-2-Substituted-5-Phenylphenazin-5-Ium Chlorides by Oxidative Cyclization

2019 ◽  
Vol 16 (2) ◽  
pp. 283-287
Author(s):  
Yuan Liu ◽  
Ling Jin ◽  
Jun-feng Liu ◽  
Yu-qi Wang ◽  
Zhi-xiang Zhou
Keyword(s):  
Reaction Time ◽  
Potassium Permanganate ◽  
Raw Materials ◽  
13C Nmr Spectroscopy ◽  
Oxidative Cyclization ◽  
Ir Absorption ◽  
Absorption Data ◽  
1H And 13C Nmr ◽  
Ft Ir ◽  
High Yields

Aim and Objective:Phenazines are substances with an extensive range of important applications. Recently, the synthesis of N-arylation has been made more feasible owing to the advent of a new methodology. But because the toxicity of the used oxidant and the low yield, it is necessary to find a nonpoisonous or less toxic oxidant. We report on the use of potassium permanganate as an oxidant to synthesize phenylphenazin-5- ium chlorides via sequential aniline arylation.Materials and Methods:The corresponding 2-substituted-3-amino-5-phenyl-7-N,N-dimethylamino phenazinium chlorides were obtained via various o-substituted toluidines reacted with 4-amino-N,N-dimethyamine and aniline using potassium permanganate as an oxidant under different conditions such as temperature, pH, reaction time and the ratio of raw materials. Infrared (IR) absorption data were acquired on a Thermo Nicolet Nexus 670 FT-IR spectrometer with DTGS KBr detector. All the products were characterized by Mass, 1H and 13C NMR spectroscopy. The total C, H, N, content was measured by the elemental analyzer.Results:The yields of 3-amino-7-(N,N-dimethylamino)-2-substituted-5-phenylphenazin-5-ium chlorides are from 42.5% to 75.8% based on the electrophilic ability of different substituted groups under the temperature of 95°C, pH 4.5 and the reaction time of 8hrs.Conclusion:3-Amino-7-(N,N-dimethylamino)-2-substituted-5-phenylphenazin-5-ium chlorides have been synthesized in high yields via the oxidative cyclization with potassium permanganate. This route is a simple, economic, efficient and environmentally friendly.

scholarly journals Ionic Liquids Based on Oxidoperoxido-Molybdenum(VI) Complexes with a Chelating Picolinate Ligand for Catalytic Epoxidation

Reactions ◽  
2020 ◽  
Vol 1 (2) ◽  
pp. 147-161
Author(s):  
Željko Petrovski ◽  
Margarida M. Antunes ◽  
Ana Soraia Mendo ◽  
Luís Cabrita ◽  
Isabel S. Gonçalves ◽  
...  
Keyword(s):  
Differential Pulse ◽  
Catalytic Performance ◽  
Model Reaction ◽  
1H And 13C Nmr ◽  
Catalytic Epoxidation ◽  
Tert Butyl Hydroperoxide ◽  
Ionic Compounds ◽  
Ft Ir ◽  
Pulse Voltammetry ◽  
High Yields

Ionic oxidoperoxido-molybdenum(VI) complexes of the type [Cat][MoO(O2)2(pic)], with pic = N,O-chelated picolinate ligand and Cat = monocation, were prepared in high yields (82–95%) from the precursor complex [H3O][MoO(O2)2(pic)] via [H]+ cation exchange for 1-ethyl-3-methylimidazolium [EMIM]+, 1-butyl-3-methylimidazolium [BMIM]+, 1-octyl-3-methylimidazolium [OMIM]+, N-cetylpyridinium [C16Py]+, and N-methyl-N,N,N-trioctylammonium [Aliquat]+. The structure and purity of the ionic compounds were assessed by 1H and 13C NMR, FT-IR, and elemental analysis (C, H, N), and the electrochemical properties were studied by differential pulse voltammetry (DPV) and cyclic voltammetry (CV). The [Cat][MoO(O2)2(pic)] compounds showed promising catalytic epoxidation activity based on the model reaction of cis-cyclooctene with tert-butyl hydroperoxide as oxidant. The type of cation influenced the physical state of the compound and the catalytic performance.

Synthesis and Characterization of Zn-Ca-Mg-Al Hydrotacite-Like Compounds and its Application in the PVC

2011 ◽  
Vol 66-68 ◽  
pp. 65-69
Author(s):  
Long Feng Li ◽  
Yuan Gao ◽  
Mao Lin Zhang
Keyword(s):  
Reaction Time ◽  
Ph Value ◽  
Raw Materials ◽  
Treatment Temperature ◽  
Molar Ratio ◽  
Medium Ph ◽  
X Ray ◽  
Ft Ir ◽  
Thermal Stability Of

Ca-Mg-Al hydrotalcite-like compounds (CaMgAl-HTLcs) were synthesized by a hydrothermal method, and characterized by X-ray powder diffraction (XRD), Fourier transform infrared spectroscopy (FT-IR) and differential thermal analysis (DTA) techniques. The effects of the medium pH value, the molar ratio of the raw materials, the reaction temperature and the reaction time on the structure of CaMgAl-HTLcs were studied. The results showed that increasing treatment temperature and reaction time could improve the crystallinity and monodispersity of hydrotalcite-like compound particles. And well-defined CaMgAl-HTLcs could be prepared at a pH value of 10~11 with n(Zn+Mg+Ca):n(Al) =2. The products synthesized were applied to PVC to improve the thermal stability of PVC.

Grinding Synthesis of Pyrazolyl-Bis Coumarinyl Methanes Using Potassium 2-Oxoimidazolidine-1,3-diide

2019 ◽  
Vol 16 (2) ◽  
pp. 303-308 ◽  
Author(s):  
Kazem Hematinezhad ◽  
Mohammad Nikpassand ◽  
Leila Zare Fekri
Keyword(s):  
Reaction Time ◽  
Room Temperature ◽  
Aqueous Media ◽  
13C Nmr Spectroscopy ◽  
Reusable Catalyst ◽  
Reduced Pressure ◽  
Elemental Analyses ◽  
Nucleophilic Addition Reaction ◽  
High Yields ◽  
Work Up

Aim and Objective: Potassium 2-oxoimidazolidine-1,3-diide (POImD) as a novel and reusable catalyst was used for the synthesis of pyrazolyl-bis coumarinyl methanes by a nucleophilic addition reaction of synthetized pyrazolecarbaldehyde and two equivalents of 4-hydroxycoumarin under grinding. The catalyst can be reused and recovered several times without loss of activity. This method provides several advantages such as eco-friendliness, simple work-up and shorter reaction time as well as excellent yields. All of the synthesized compounds were characterized by IR, 1H and 13C NMR spectroscopy and elemental analyses. Material and Method: Synthetized pyrazole carbaldehyde 1a (1 mmol), 4-hydroxycoumarin 2 (2 mmol), 1 mmol of POImD and 10mL of H2O were ground in a mortar by a pestle for 30-90 minutes. After the completion of the reaction, as monitored by TLC on silica gel using ethyl acetate/n-hexane (1:2), the mixture was allowed to cool to room temperature. After completion of the reaction, we extracted the product with CH2Cl2/H2O. This was followed by separation of phases, evaporation of the organic phase and recrystallization of the residue with 50 mL of ethanol/H2O (1:1). The pure product was then obtained in 87 to 96% yield. The aqueous phase was concentrated under reduced pressure to recover the catalyst for subsequent use. Results: To continue our ongoing studies to synthesize heterocyclic and pharmaceutical compounds by mild, facile and efficient protocols, herein we wish to report our experimental results on the synthesis of pyrazolylbis coumarinyl methanes, using various synthetized pyrazole carbaldehydes and 4-hydroxycoumarin in the presence of POImD in aqueous media at room temperature. Conclusion: Finally, we developed an efficient, fast and convenient procedure for the three-component synthesis of pyrazolyl-bis coumarinyl methanes through the reaction of pyrazole carbaldehydes and 4- hydroxycoumarin, using POImD as a novel and reusable catalyst. The remarkable advantage offered by this method is that the catalyst is non-toxic, inexpensive, easy to handle and reusable. A short reaction time, simple work-up procedure, high yields of product with better purity and the green aspect by avoiding a hazardous solvent and a toxic catalyst are the other advantages. To the best of our knowledge, this is the first report on the synthesis of pyrazolyl-bis coumarinylmethane derivatives using potassium 2-oxoimidazolidine-1,3-diide (POImD).

scholarly journals Research on the Preparation and Performance of Binary Modified Maltodextrin Water-Reducing Agent

2016 ◽  
Vol 2016 ◽  
pp. 1-6
Author(s):  
Jingzhi Wu ◽  
Min Qiao ◽  
Zhifeng Lyu ◽  
Qianping Ran
Keyword(s):  
Reaction Time ◽  
Raw Materials ◽  
Reducing Agent ◽  
Optimal Conditions ◽  
Catalyst Amount ◽  
Dextrose Equivalent ◽  
Ft Ir ◽  
Dispersion Capacity ◽  
Anchoring Groups ◽  
And Performance

Using maltodextrin (MD) of different dextrose equivalent (DE) values, 1,3-propanesultone, and maleic anhydride as raw materials, a novel binary modified maltodextrin (BMMD) was synthesized and further applied as a water-reducing agent. Its structure was characterized by Fourier transform infrared (FT-IR) and UV. The rheological behavior of the sample solution and strengths for concrete were also determined and the adsorption was tested by TOC. The influence of the process parameters to degree of substitution (DS) and the dosage on the fluidity of cement paste were investigated. The results show that the optimal conditions of sulfonation were the MD of DE 15, m (sulfonated agent)/m (MD) of 1.4, the catalyst amount of 1% by mass MD, and the reaction time of 12 h; the optimal conditions of esterification were m (esterified agent)/m (SMD) of 0.6, the reaction temperature of 90°C, and the reaction time of 4 h. The optimal dosages of sulfonated maltodextrin (SMD) and BMMD were 0.475% and 0.45%, respectively. In this dosage, the main dispersion capacity of BMMD attributes to two kinds of anchoring groups (SO3-  &  COO-) and the appropriate molecular weight of MD.

scholarly journals Study on the Microwave-Assisted Batch and Continuous Flow Synthesis of N-Alkyl-Isoindolin-1-One-3-Phosphonates by a Special Kabachnik–Fields Condensation

Molecules ◽  
2020 ◽  
Vol 25 (14) ◽  
pp. 3307
Author(s):  
Ádám Tajti ◽  
Nóra Tóth ◽  
Bettina Rávai ◽  
István Csontos ◽  
Pál Tamás Szabó ◽  
...  
Keyword(s):  
Reaction Time ◽  
Continuous Flow ◽  
Molar Ratio ◽  
Primary Amines ◽  
Diethyl Phosphite ◽  
The Novel ◽  
Dialkyl Phosphites ◽  
Ft Ir ◽  
High Yields ◽  
Real Time Information

A simple and efficient microwave (MW)-assisted method was elaborated for the catalyst-free synthesis of isoindolin-1-one-3-phosphonates by the three-component condensation of 2-formylbenzoic acid, aliphatic primary amines and various dialkyl phosphites. The batch and the continuous flow reactions were optimized in respect of the temperature, the reaction time and the molar ratio of the starting materials. To evaluate the potential of MW irradiation, comparative thermal experiments were also carried out. In order to obtain “real time” information about the condensation, the special Kabachnik–Fields reaction of 2-formylbenzoic acid, butylamine and diethyl phosphite was monitored by in situ FT-IR spectroscopy. The novel title compounds could be prepared in high yields at low temperature under a short reaction time. A suitable method could also be developed for the preparation of the isoindolin-1-one-3-phosphonates at a “few g” scale by using a continuous flow MW reactor.

scholarly journals Synthesis, Thermal and Optical Characterizations of New Lateral Organic Systems

Crystals ◽  
2021 ◽  
Vol 11 (5) ◽  
pp. 551
Author(s):  
Laila Ahmed. Al-Mutabagani ◽  
Latifah A. Alshabanah ◽  
Sobhi M. Gomha ◽  
Hoda A. Ahmed
Keyword(s):  
Methoxy Group ◽  
13C Nmr Spectroscopy ◽  
Molecular Structures ◽  
Phenyl Ester ◽  
Scanning Calorimetry ◽  
1H And 13C Nmr ◽  
Polarized Optical Microscopy ◽  
Organic Systems ◽  
Temperature Ranges ◽  
Ft Ir

New laterally OCH3-substituted optical organic Schiff base/ester series, namely 4-(4-(hexyloxyphenyl)iminomethyl)-3-methoxyphenyl 4-alkoxybenzoates, were prepared and characterized with different thermal, mesomorphic, and photoactive techniques. The prepared group constitutes five homologues that differ from each other in the number of carbons in the terminal alkoxy chain (n), which varies between n = 6, 8, 10, 12, and 16 carbons. The laterally protruded methoxy group is attached to the central benzene ring that makes an angle of 120° with the molecular long axis. Molecular structures of all newly prepared homologues were fully elucidated via FT-IR, 1H and 13C NMR spectroscopy. Mesomorphic transitions were determined via differential scanning calorimetry (DSC) and the phases identified by polarized optical microscopy (POM). Independent of the length of the terminal alkoxy chain attached to phenyl ester ring, only a monomorphic nematic (N) phase was observed for all the synthesized compounds. A comparative study was made between the present lateral methoxy-substituted homologues and their corresponding laterally-neat analogues. The results revealed that, depending on the length of the alkoxy chain and the presence or absence of the lateral methoxy group, different mesophases with different thermal stability and temperature ranges were observed. Finally, UV-vis spectra showed that the present nematogenic series possess photoactive properties that are of importance for many applications.

scholarly journals FACILE SYNTHESIS OF PHENOLIC DERIVATIVES, CONTAINIG LACTAMOMETHYL SUBSTITUENTS

2019 ◽  
Vol 62 (10) ◽  
pp. 40-48
Author(s):  
Stepan V. Vorobyev ◽  
Olga V. Primerova ◽  
Ludmila V. Ivanova ◽  
Vladimir D. Ryabov ◽  
Vladimir N. Koshelev
Keyword(s):  
13C Nmr Spectroscopy ◽  
Hydroxyl Group ◽  
1H And 13C Nmr ◽  
Mineral Oils ◽  
Ft Ir ◽  
Low Toxicity ◽  
Phenolic Derivatives ◽  
Intramolecular Hydrogen ◽  
Derivatives Of ◽  
Low Solubility

In this work we suggest the new method for the synthesis of novel phenolic derivatives, containing lactamomethyl substituents. Oxidation processes of fuels and mineral oils lead to losing of their properties, so the search for new and effective inhibitors of these processes is very actuel. We suggest a facile system for lactamomethylation reaction. Heating in the water some of phenols (resorcinol, phloroglucinol, methylphloroglucinol, pyrogallol, salicylic, resorcilic and gallic acids) with N-hydroxymethyl derivatives of pyrrolidone, valerolactam, caprolactam and 4-phenylpyrrolidone in the presence of catalytic amounts of acetic acid led to the target compounds with nearly quantitative yields. Time of the reaction ranged 1.5-2 h. As the products have low solubility in water, in contrast with the reagents, filtration was used for their extraction. The advantages of this method are also that it is eco-friendly because of small amounts of wastes and low toxicity of the reagents and solvent, and cheapness of starting compounds. Eighteen novel compounds were obtained. The composition of target substances was determined by elemental analysis whereas the structures of the synthesized compounds were confirmed by FT-IR spectroscopy methods, 1H- and 13C-NMR spectroscopy. In IR spectra there are carbonyl group stretching vibrations peaks in lower frequencies (about 1600 cm-1) than expected due to the formation of inter- and intramolecular hydrogen bonds between this group and phenolic hydroxyl group.

scholarly journals N-[2-(1H-Indol-3-yl)-1-(5-thioxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)ethyl]-4-methylbenzenesulfonamide

Molbank ◽  
10.3390/m1008 ◽  
2018 ◽  
Vol 2018 (3) ◽  
pp. M1008
Author(s):  
Nikil Purushotham ◽  
Boja Poojary
Keyword(s):  
Mass Spectrometry ◽  
Mycobacterium Tuberculosis ◽  
Potassium Hydroxide ◽  
Inhibitory Action ◽  
13C Nmr Spectroscopy ◽  
Enoyl Reductase ◽  
1H And 13C Nmr ◽  
Ft Ir ◽  
Non Covalent Interactions ◽  
Covalent Interactions

N-[1-Hydrazinyl-3-(1H-indol-3-yl)-1-oxopropan-2-yl]-4-methylbenzenesulfonamide (1) on cyclization with carbon disulfide in ethanolic potassium hydroxide affords N-[2-(1H-indol-3-yl)-1-(5-thioxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)ethyl]-4-methylbenzenesulfonamide (2) in 84% yield. The structure of compound 2 was supported by mass spectrometry, FT-IR and 1H- and 13C-NMR spectroscopy. To investigate the potential of compound 2 to act as antitubercular agent, it was docked against the enoyl reductase (InhA) enzyme of Mycobacterium tuberculosis. The docking pose and non-covalent interactions gave insights on its plausible inhibitory action.

Preparation and Characterization of Magnesium Borate Whisker

2013 ◽  
Vol 662 ◽  
pp. 481-484
Author(s):  
Zhi Liang Jin ◽  
Xu Jing ◽  
Yuan Hong ◽  
Xue Ying Nai ◽  
Li Wu
Keyword(s):  
Reaction Time ◽  
Molten Salt ◽  
Reaction Temperature ◽  
High Performance ◽  
Raw Materials ◽  
Price Ratio ◽  
Magnesium Borate ◽  
Synthesis Conditions ◽  
Ft Ir

Being a new whisker products with high performance to price ratio, magnesium borate whiskers with a length of 10 - 50μm and a diameter of 0.5 - 2μm were prepared by molten salt and characterized by XRD, FT - IR, SEM and chemical titration. The experiments show that the synthesis conditions are as follows: raw materials ratio: Mg:B:flux =1:11.05:1-3.5(mol); reaction temperature: 800 - 950°C;reaction time:6 - 10hours; flux: NaCl、KCl or NaOH.

3-Amino-2-methylquinazolin-4-(3H)-one Schiff Bases Synthesis – a Green Chemistry Approach – a Comparison of Microwave and Ultrasound Promoted Synthesis with Mechanosynthesis.

2020 ◽  
Vol 07 ◽  
Author(s):  
Mario Komar ◽  
Fran Prašnikar ◽  
Tatjana Gazivoda Kraljević ◽  
Krunoslav Aladić ◽  
Maja Molnar
Keyword(s):  
Mass Spectrometry ◽  
Green Chemistry ◽  
Schiff Bases ◽  
13C Nmr Spectroscopy ◽  
Synthetic Methods ◽  
Reaction Conditions ◽  
1H And 13C Nmr ◽  
Microwave Assisted ◽  
Ultrasound Assisted ◽  
High Yields

: A green chemistry methods are important modern pathways in synthetic chemistry with main advantages such as milder reaction conditions, shorter time and higher yields. A series of quinazolinone based Schiff bases (1−27) have been successfully synthesized by using green synthetic methods including microwave-assisted, ultrasound-assisted and mechanochemical synthesis, respectively. Desired compounds were prepared from 3-amino-2-methylquinazolin-4(3H)- one and substituted benzaldehydes with moderate to high yields (11−90%). Benzoxazinone and 3-amino-2- methylquinazolin-4(3H)-one, the precursors of Schiff bases, were prepared by microwave induced synthesis. The structures of all Schiff bases are confirmed by 1H and 13C NMR spectroscopy and mass spectrometry as well. A novelty of this research is the application and comparison of green chemistry methods in the synthesis of desired compounds are listed above. The simplicity of synthesis includes ethanol as solvent and no need for further purification.

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